Fwiw, part of the reason I moved to Dallas instead of Austin back in 2020 was due to one of the WSP city guide posts from 2018/2019.
Absolutely no way I would recommend Houston on your list though for the given persona. Insanely spread out (same complaint as LA), bad social/dating scene (partly due to being spread out), & terrible weather. Not the worst place though if you're looking for cheap housing for a family in the burbs. My 2c.
I'm sure there are lots of people that read BTB that live in each city, that know the details only a local would know. Example: having grown up, moved around different areas and worked in Toronto, I know the city like the back of my hand and can speak first hand to why someone may want to come here (or not), and how to make the most if you're coming for an extended stay.
Would love to talk about Singapore or Hong Kong as well, having spent the last decade working between both.
Just to keep this relatively short, it depends on why you’re moving there.
Having grown up there, Toronto is a place that tries to be like New York, London, or other major metropolitan cities. It draws people from all over Canada who’ve never seen the “big city”, but internationally, it’s not that significant in the grand scheme of things. There’s a bit of an “Equities in Dallas” or “Failed in London, try Hong Kong” kind of feel to it, but there is an attempt at being a major international city. It’s not materialistic as LA or Miami, and it’s probably one of the best places on earth to raise a family, but there are a lot of tradeoffs to be aware of.
- Pros
- Fairly decent medical system for free/next to free (relative to the neighbours in the south)
- Fairly decent public education system. If your kids are going to college “in province” the fees are much lower than the US counterparts - and some of the best universities in Canada are in/around Toronto.
- There’s a lot of great food, particularly international food. I took it for granted how good food was in Toronto until I moved to New York and realized that not all cities have food that good. The food scene is probably the best in any city in North America, bar none. In particular, here’s a list of casual places off top of head:
- Chinese food - go up to Markham, or even in Chinatown (there’s more than I can list, but particularly memorable is Fisherman’s Clubhouse in Markham)
- Korean food - best I’ve ever had next to Korea (try Owl of Minerva (24x7) or BCD tofu house) in Korea town near Bloor and Bathurst or Ka Chi all around the city
- Greek food - try Astoria or Messini’s in Greek town (Danforth, east of DVP). They’re institutions. Do drop by again for Taste of the Danforth, but not opening night, and hopefully on a day it rains so the crowds thin out a bit
- Indian food - some of the best next to London. Try Ghandi Roti on Queen and Bathurst (I think it closed during the Pandemic but was bought out by the workers and renamed itself with the same menu)
- Vietnamese Pho - UFO restaurant, Pho Hung
- Toronto Street dogs are amazing. Ignore the dinky, watery New York hot dog. Get a good Italian or polish sausage on a bun, particularly after a night of heavy drinking.
- Lots of interesting areas to check out.
- Kensington market / Distillery district (indie-ish area with lots of coffee shops and restaurants)
- King West/Queen West/Parkdale - “the Meatpacking” of Toronto. All the fashionable restaurants/clubs/startups are here
- Harbourfront - walk/bike along the Toronto Harbour, lots of parks and things to do
- Toronto Islands - take a ferry across to a kids amusement park, some restaurants, some beaches and parks
- The Beaches - one of the largest public beaches with beach volleyball, picnic spaces, etc.
- Toronto prides itself on parks and green spaces, and there are a lot of spaces throughout the city. You can walk up a park from downtown to up town via the DVP, there’s various conservation areas
- There’s a fairly popular arts/live music scene, but I’ve probably been gone too long to comment on what’s happening.
- Cons
- Prevailing wage is much lower than in the US, particularly for fields like law/finance/tech, and your career growth will be much slower than in a London/Hong Kong/New York because there isn’t that much competition or opportunity. People tend to stagnant in their careers. You’re also getting paid in CAD which is worth like 75 cents on the USD. The consequence of this is that the best and the brightest tend to leave for greener pastures. It’s a great place if you’re looking for a retirement gig and want to focus on your family or wifi money or something else, but if you’re young, ambitious and motivated, it’s not the place to be.
- Things tend to be a bit more expensive than the US. The cost of living, adjusted for incomes is really bad. It’s hard to build wealth here. The tax rate is also quite high and rising, it’s quite similar to California and New York
- Crime is getting worse, feels a bit like NYC, but not as bad as SF/LA yet.
- Housing costs are astronomical relative to incomes. Renting costs have been skyrocketing, and speculation on real estate is the local pastime. I suggest not looking to buy if you’re not planning to be there forever, the numbers really don’t work out. The laws are very tenant friendly as well - basically it’s impossible to kick you out legally unless they’re moving themselves in, and even so they have to compensate you a few months rent. Also, there’s rent stabilization on any unit completed before roughly 2018.
- People tend to be a bit snobby. People that grew up there tend to have their cliques and I found it much harder to make new friends relative to countries with significant in and out migration like New York/London/Hong Kong. Status is a big thing to people, and it’s one of those cities where the first thing people ask you is what you do in order to size you up
- Other
- Both a Pro/Con depending on how you look at it. Toronto has a very strong car culture. It’s possible to live without a car, particularly in downtown, but it makes life very inconvenient. There is public transit (TTC/Go Train), but it isn’t amazing. Drivers are also a bit crap. I’d strongly, strongly recommend a car for everyone, but especially if you’re not in downtown or directly on top of the subway line. Especially during winter, where it’s wet and slushy outside, it’s pretty miserable trying to get around via public transport. Taxis tend to be expensive and rip you off, Uber is okay.
Depending on your situation - are you young and single, or are you moving with family, and how long you intend to be there, we can talk about different areas to look for homes, and what to expect.
Wow, incredibly helpful and generous advice. Really appreciate it!
My partner is from the region, so prime reason for moving is so she can be closer to friends and family, while we settle down and start a family of our own. No kids yet so looking at living around Queen West initially. Medium term horizon at this stage. A lot of the things you’re saying resonate with my limited experiences so far. I’m relocating from London where I’m also an expat, so have noticed many of the pros and cons vs London and where I’m from, a much warmer part of the world
I'm honestly surprised that BTB is so focused on cities. I mean I get it - people want to feel connected and have fun. But if you're making wifi and crypto monies, is it really better to live in NYC or LA than on a 10 acre spread right outside a small 10,000 person town where you can work from your cheap, 6 bedroom farmhouse, own and shoot all the guns you want, sweet talk the farmers' daughters (and marry one who wants to be a stay at home wife and raise your kids), and drink 25 year old scotch and smoke cubans at the one cigar bar on Main Street? Feels like that would be a better option than trying to survive NYC so that you can eat at Spago and do shots with thots.
2c on TX cities: We know people from all 3 cities and we're in Houston. Austin not worth it IMO. Generally, I recommend Dallas, especially if you want to buy a home now, prob good price appreciation.
Houston isn't worth it unless you're already planning kids/family. Houston is an easy place to "live", but crappy place to visit - feels like the anti-NYC. Dating scene sucks and spread out. Food scene is diverse and excellent quality/$, but NYC has much more 5-star spots, so we'd go visit NYC instead. Social scene casual vibe vs Dallas/NYC status-conscious.
Good for home/kids/labor cost, top medical facilities - rich Europeans fly over for MD Anderson. No zoning laws = less cleaner look than Dallas, meh geography, humidity turns people off, lots of land to build out - keeps home prices/property taxes low.
TLDR Background: In 30s, originally from East Coast - but moved young to cut costs on college for in-state TX tuition. L4 Google eng ~300k TC @ Houston - planning a gamble on big O&G cloud/ML opportunity by gathering rolodex with cloud sales, doing ML-adjacent DevOps while taking MS CS to capitalize on "AI". Met SO in Austin way back (UT Austin CS, I guess we're autists) but we moved ASAP when homeless problem worsened almost a decade ago. Also building out AUM-based RIA & bookkeeping biz, currently at ~100k net revenue - I do operations, algo/research (arb & NLP strategy), some initial sales. Biz partner does compliance, most of sales, "handholding"/financial planning. Decent growth on boring old business model with tech-refreshments and lower labor costs. Bought a few multifamily with 2%+/mo rent revenue in outskirts. Been following since old WSP blog, can vouch for old Triangle Investing book - still works.
Chicago suburbs are better than most because all trains run through Chicago and hence many, many suburbs have walkable downtowns which means ability to walk to friends’ houses etc. Chicago however is a heartbreaker.
Consider Taipei and Orange County. OC has different vibe than LA. Safer as well (mostly). I grew up in Vancouver and travel there multiple times a year. Happy to provide my insight.
Good stuff as always. I’m a little surprised to see Santo Domingo and Punta Cana on the list. What are your thoughts on investing in RE long term there?
I know is not a Q&A forum, but it would be interesting to hear your opinion. In summary, the RE is growing by double digits every year and cap rates are attractive. For that reason, it is a little hard to ignore since other comps like Cancun and Hawaii are 5x-10x Punta Cana prices.
1. Can we get Octopod to chime in with restaurant recs in each city? 👀
2. Any small towns in USA ever stand out enough to mention? Outside of typical "nice place to raise kids"
If he can comment sure he will
BowtiedEscobar over here with the exhaustive deep dive into Colombian cities. 🤪. Looking forward to these should be fun.
Fwiw, part of the reason I moved to Dallas instead of Austin back in 2020 was due to one of the WSP city guide posts from 2018/2019.
Absolutely no way I would recommend Houston on your list though for the given persona. Insanely spread out (same complaint as LA), bad social/dating scene (partly due to being spread out), & terrible weather. Not the worst place though if you're looking for cheap housing for a family in the burbs. My 2c.
Yep.
How can we (the jungle) help?
I'm sure there are lots of people that read BTB that live in each city, that know the details only a local would know. Example: having grown up, moved around different areas and worked in Toronto, I know the city like the back of my hand and can speak first hand to why someone may want to come here (or not), and how to make the most if you're coming for an extended stay.
Would love to talk about Singapore or Hong Kong as well, having spent the last decade working between both.
Sure when you see the structure you can come up with one just ping us via email
Moving there in 2 months... any tips?
Which one? Toronto, Hong Kong or Singapore?
Realised I was completely unclear after I wrote my comment 🤦🏻♂️ Toronto
Just to keep this relatively short, it depends on why you’re moving there.
Having grown up there, Toronto is a place that tries to be like New York, London, or other major metropolitan cities. It draws people from all over Canada who’ve never seen the “big city”, but internationally, it’s not that significant in the grand scheme of things. There’s a bit of an “Equities in Dallas” or “Failed in London, try Hong Kong” kind of feel to it, but there is an attempt at being a major international city. It’s not materialistic as LA or Miami, and it’s probably one of the best places on earth to raise a family, but there are a lot of tradeoffs to be aware of.
- Pros
- Fairly decent medical system for free/next to free (relative to the neighbours in the south)
- Fairly decent public education system. If your kids are going to college “in province” the fees are much lower than the US counterparts - and some of the best universities in Canada are in/around Toronto.
- There’s a lot of great food, particularly international food. I took it for granted how good food was in Toronto until I moved to New York and realized that not all cities have food that good. The food scene is probably the best in any city in North America, bar none. In particular, here’s a list of casual places off top of head:
- Chinese food - go up to Markham, or even in Chinatown (there’s more than I can list, but particularly memorable is Fisherman’s Clubhouse in Markham)
- Korean food - best I’ve ever had next to Korea (try Owl of Minerva (24x7) or BCD tofu house) in Korea town near Bloor and Bathurst or Ka Chi all around the city
- Greek food - try Astoria or Messini’s in Greek town (Danforth, east of DVP). They’re institutions. Do drop by again for Taste of the Danforth, but not opening night, and hopefully on a day it rains so the crowds thin out a bit
- Indian food - some of the best next to London. Try Ghandi Roti on Queen and Bathurst (I think it closed during the Pandemic but was bought out by the workers and renamed itself with the same menu)
- Vietnamese Pho - UFO restaurant, Pho Hung
- Toronto Street dogs are amazing. Ignore the dinky, watery New York hot dog. Get a good Italian or polish sausage on a bun, particularly after a night of heavy drinking.
- Lots of interesting areas to check out.
- Kensington market / Distillery district (indie-ish area with lots of coffee shops and restaurants)
- King West/Queen West/Parkdale - “the Meatpacking” of Toronto. All the fashionable restaurants/clubs/startups are here
- Harbourfront - walk/bike along the Toronto Harbour, lots of parks and things to do
- Toronto Islands - take a ferry across to a kids amusement park, some restaurants, some beaches and parks
- The Beaches - one of the largest public beaches with beach volleyball, picnic spaces, etc.
- Toronto prides itself on parks and green spaces, and there are a lot of spaces throughout the city. You can walk up a park from downtown to up town via the DVP, there’s various conservation areas
- There’s a fairly popular arts/live music scene, but I’ve probably been gone too long to comment on what’s happening.
- Cons
- Prevailing wage is much lower than in the US, particularly for fields like law/finance/tech, and your career growth will be much slower than in a London/Hong Kong/New York because there isn’t that much competition or opportunity. People tend to stagnant in their careers. You’re also getting paid in CAD which is worth like 75 cents on the USD. The consequence of this is that the best and the brightest tend to leave for greener pastures. It’s a great place if you’re looking for a retirement gig and want to focus on your family or wifi money or something else, but if you’re young, ambitious and motivated, it’s not the place to be.
- Things tend to be a bit more expensive than the US. The cost of living, adjusted for incomes is really bad. It’s hard to build wealth here. The tax rate is also quite high and rising, it’s quite similar to California and New York
- Crime is getting worse, feels a bit like NYC, but not as bad as SF/LA yet.
- Housing costs are astronomical relative to incomes. Renting costs have been skyrocketing, and speculation on real estate is the local pastime. I suggest not looking to buy if you’re not planning to be there forever, the numbers really don’t work out. The laws are very tenant friendly as well - basically it’s impossible to kick you out legally unless they’re moving themselves in, and even so they have to compensate you a few months rent. Also, there’s rent stabilization on any unit completed before roughly 2018.
- People tend to be a bit snobby. People that grew up there tend to have their cliques and I found it much harder to make new friends relative to countries with significant in and out migration like New York/London/Hong Kong. Status is a big thing to people, and it’s one of those cities where the first thing people ask you is what you do in order to size you up
- Other
- Both a Pro/Con depending on how you look at it. Toronto has a very strong car culture. It’s possible to live without a car, particularly in downtown, but it makes life very inconvenient. There is public transit (TTC/Go Train), but it isn’t amazing. Drivers are also a bit crap. I’d strongly, strongly recommend a car for everyone, but especially if you’re not in downtown or directly on top of the subway line. Especially during winter, where it’s wet and slushy outside, it’s pretty miserable trying to get around via public transport. Taxis tend to be expensive and rip you off, Uber is okay.
Depending on your situation - are you young and single, or are you moving with family, and how long you intend to be there, we can talk about different areas to look for homes, and what to expect.
Wow, incredibly helpful and generous advice. Really appreciate it!
My partner is from the region, so prime reason for moving is so she can be closer to friends and family, while we settle down and start a family of our own. No kids yet so looking at living around Queen West initially. Medium term horizon at this stage. A lot of the things you’re saying resonate with my limited experiences so far. I’m relocating from London where I’m also an expat, so have noticed many of the pros and cons vs London and where I’m from, a much warmer part of the world
Looking forward to the guides
Only missed buenos aires, since it is a nice city and even easier to enjoy expensive stuff nowadays
Any tips? Probably going later this year
Not much, been there for a week only this year
Look into palermo, recoleta and puerto madero fpr the good stuff
And check out @bowtiedmara
I'm honestly surprised that BTB is so focused on cities. I mean I get it - people want to feel connected and have fun. But if you're making wifi and crypto monies, is it really better to live in NYC or LA than on a 10 acre spread right outside a small 10,000 person town where you can work from your cheap, 6 bedroom farmhouse, own and shoot all the guns you want, sweet talk the farmers' daughters (and marry one who wants to be a stay at home wife and raise your kids), and drink 25 year old scotch and smoke cubans at the one cigar bar on Main Street? Feels like that would be a better option than trying to survive NYC so that you can eat at Spago and do shots with thots.
2c on TX cities: We know people from all 3 cities and we're in Houston. Austin not worth it IMO. Generally, I recommend Dallas, especially if you want to buy a home now, prob good price appreciation.
Houston isn't worth it unless you're already planning kids/family. Houston is an easy place to "live", but crappy place to visit - feels like the anti-NYC. Dating scene sucks and spread out. Food scene is diverse and excellent quality/$, but NYC has much more 5-star spots, so we'd go visit NYC instead. Social scene casual vibe vs Dallas/NYC status-conscious.
Good for home/kids/labor cost, top medical facilities - rich Europeans fly over for MD Anderson. No zoning laws = less cleaner look than Dallas, meh geography, humidity turns people off, lots of land to build out - keeps home prices/property taxes low.
TLDR Background: In 30s, originally from East Coast - but moved young to cut costs on college for in-state TX tuition. L4 Google eng ~300k TC @ Houston - planning a gamble on big O&G cloud/ML opportunity by gathering rolodex with cloud sales, doing ML-adjacent DevOps while taking MS CS to capitalize on "AI". Met SO in Austin way back (UT Austin CS, I guess we're autists) but we moved ASAP when homeless problem worsened almost a decade ago. Also building out AUM-based RIA & bookkeeping biz, currently at ~100k net revenue - I do operations, algo/research (arb & NLP strategy), some initial sales. Biz partner does compliance, most of sales, "handholding"/financial planning. Decent growth on boring old business model with tech-refreshments and lower labor costs. Bought a few multifamily with 2%+/mo rent revenue in outskirts. Been following since old WSP blog, can vouch for old Triangle Investing book - still works.
Would love to see a write up of El Salvador considering us Bitcoiners may have to flee there one day when the US goes full communist
Very excited for this
Love Las Vegas. Great weather. Highly convenient. Relatively cheap. Like living in California without having to live in California.
I'm curious if you'll be doing a guide on the Tampa bay area since it's been referenced every once in a while.
Chicago suburbs are better than most because all trains run through Chicago and hence many, many suburbs have walkable downtowns which means ability to walk to friends’ houses etc. Chicago however is a heartbreaker.
Consider Taipei and Orange County. OC has different vibe than LA. Safer as well (mostly). I grew up in Vancouver and travel there multiple times a year. Happy to provide my insight.
can you also breakdown best areas to live in each city for age ranges/dating/nightlife/safety
Impossible we just give rough ranges on what to do at budget level
Good stuff as always. I’m a little surprised to see Santo Domingo and Punta Cana on the list. What are your thoughts on investing in RE long term there?
I know is not a Q&A forum, but it would be interesting to hear your opinion. In summary, the RE is growing by double digits every year and cap rates are attractive. For that reason, it is a little hard to ignore since other comps like Cancun and Hawaii are 5x-10x Punta Cana prices.
We already said we can't do international RE because we don't know enough about the laws/rules
Dubai not on the list ? 👀