Your City Pairs

[Omaharocks]

Now that me and my wife are both potentially veering towards permanent remote work, we've been thinking of where we want to be, and increasingly are considering finding a way to live part of the year in one place and part of the year in another.

There are of course practical considerations. We'd need to be able to afford it, possibly by renting out one or some duplex rent one/own one situation, so real estate can't be insanely expensive. We'd like to be near family in one of the locations, ideally summer when our kid isn't in school, and it only makes sense for them to be in different climates. I think it'd also be best if they were substantially different size-wise and culturally so they complement each other.

This has gotten me thinking about 1) Practical city pairs, and 2) Dream city pairs.

Practical city pairs we're looking at:

- Tucson or Albuquerque for fall/winter/spring (job and current homes are in sw)
- Milwaukee or Chicago for summer (affordable, hard to beat these places in the summer, and they are urban so complement the southwest well)

Dream city pairs (North America)

- New Orleans for winter/spring
- Montreal for summer/fall

Anywhere in the world

- Greek Islands (fall/winter)
- Montreal (spring/summer)

What are yours? Do you already live in 2 places? Would you choose differently if those two places could be anywhere?

[SFBruin]

Practical city pairs:

Seattle and Seattle (already live here)
Bay Area and Bay Area (probably only other place where I know a critical mass of people)

Dream city pairs:

Boston (summer) and San Diego (winter)

[Pedestrian]

Originally Posted by Omaharocks

What are yours? Do you already live in 2 places? Would you choose differently if those two places could be anywhere?

Yes. San Francisco in late spring through early fall; Tucson, Arizona in late fall through early spring.

I like fresh air and moderate temperatures--so I can keep the windows open and not need much heating or air-conditioning. San Francisco rarely gets much above 70 degrees in summer (and the maritime climate usually keeps the temperature within a 24-hour range of around only 10 degrees F) whereas Tucson in winter usually hits a high around 65 or 70 in the daytime but can get quite cold at night (which allows for a nice cozy fire if you want one). Tucson is also surrounded by mountains that often get snow on them in winter and there's even a smallish ski resort on top of the peaks that dominate the city. That means in theory you can ski in the morning and then play a nice round of golf wearing no more than a light jacket (or no jacket) in the afternoon. You can also have lunch in Mexico if you want (in more normal, covid-free times).

For the winter, Palm Springs might be an alternative and I know some people who go there but I like having a place outside California that gives me the option of switching "residences" for tax purposes if CA gets too ridiculous. Another option would be going a little farther to someplace like Santa Fe or Silver City, New Mexico but those are colder: Better skiing, not such great golfing.

In terms of being different, I call Tucson the "anti-San Francisco". That's not so much because of politics because Tucson is in the bluest part of AZ (mostly because of the U. of AZ being there but also a lot of midwestern transplants), but rather because you just don't encounter the urban "grit" you do in really big cities (even though the metro has a million people). I once got panhandled in a Tucson gas station while filling my tank and I couldn't help literally laughing at the poor guy. It was just that I am so used to being panhandled by San Francisco's hard core homeless he seemed like an "amateur". And one rarely sees graffiti or other evidences of grit.

[SFBruin]

Originally Posted by Pedestrian

you just don't encounter the urban "grit" you do in really big cities

Dang, less grit would be nice. I second this viewpoint.

[iheartthed]

I think about this a lot... In all scenarios, NYC would be my base.

Places where I have thought about a winter home:

-Southern California: San Diego, L.A., or Palm Springs. The major draw back, besides expense, would be time zone.

-Brazil: Somewhere along the coast in either the state of Rio de Janeiro (somewhere around Buzios to be specific), or the state of Bahia near Salvador. Time zone would actually be favorable here, since most of South America is two hours ahead of the U.S. east coast during northern winter.

-Argentina: less attractive for a winter home than Brazil because of climate, but I would consider Buenos Aires. See above for time zone.

-Puerto Rico: I need to explore PR a lot more, but I would consider a winter house there in one of the coastal areas of the main island other than San Juan. Would also consider something on the islands of Culebra or Vieques, but I need to actually see those places in person. Time zone is ideal, since PR is in the eastern time zone.

-USVI: Never been to US Virgin Islands, but the selling points would be similar to Puerto Rico. PR might have the edge due to its size, but that could also be a negative.

-Other maybes in the Caribbean: Bahamas and Barbados. Both easy to get to from U.S. mainland, relatively good infrastructure, relatively safe, and same time zone as U.S. east coast.

Places where I have considered a summer home:

-Greek Islands in the Cyclades: I've been to the Greek islands a few times during summer and it's a pretty ideal way to spend the summer for me. The only drawback to me is really the time difference from the U.S.

-Catskills or Berkshires: much more realistic. This could also be used for quick getaways in the winter, especially for skiing.

-Northern/northwestern Michigan: I have thought about looking for a vacation house near a nice lake in the northwest lower peninsula. Time zone is a plus. It would also be easier to see family in Detroit during the summer.

[Centropolis]

for me: st. louis fall and winter until after Christmas but before New Years, sonoma county, ca/north bay winter and spring, chicago summer.

so, a triumvirate of three metro areas.

[SIGSEGV]

Gets too hot in summer in Chicago, though it's fun. Maybe Anchorage would be a good respite?

[JManc]

Houston in the cooler months, Upstate NY in the warmer months through the fall. We're actually looking at property up there once the RE market cools off.

[mr1138]

I have always thought it would be awesome to keep living in Denver but have a second home in a mountain town with lots of access to hiking and skiing - somewhere like Breckenridge, Grand Lake, or Glenwood Springs.

In summer, spend each week in the mountains and come to Denver Friday-Sunday. In the winter reverse that - spend each week in the city and the weekends in the mountains.

Dream pairs though might be: Chicago in summer and fall and SF in winter and spring. International: Amsterdam in summer and fall, Rome in the winter and spring

[Pedestrian]

Originally Posted by mr1138

Dream pairs though might be: Chicago in summer and fall and SF in winter and spring. International: Amsterdam in summer and fall, Rome in the winter and spring

???? Chicago has periodic brutal summer heat waves and SF in winter can be as drippy as Seattle's reputation. It just depends whether the Pacific storm systems stay north or shift a little south and that seems to have to do with El Niño and all that stuff. Basically the California coastal rainy season runs from mid October to the end of April. Some years are quite dry (La Niña) and others are wet with rain as often as 3 days a week and not hard rain mostly--just gray and drippy. It's what I go to Arizona to escape.

On the other hand, it really never does rain in (northern OR southern) California May through September and it's cool as well.

Originally Posted by SIGSEGV

Gets too hot in summer in Chicago, though it's fun. Maybe Anchorage would be a good respite?

Today's predicted high in Anchorage: 68
Today's predicted high in San Francisco: 67

[SFBruin]

Fairbanks in the winter and Needles in the summer would be a fun transition. :-)

[Camelback]

Originally Posted by SFBruin

Practical city pairs:

Seattle and Seattle (already live here)
Bay Area and Bay Area (probably only other place where I know a critical mass of people)

Dream city pairs:

Boston (summer) and San Diego (winter)

Your dream is to do sticky humid Boston in the summer? And chilly cool San Diego in the winter?

I would do San Diego in the summer, Boston in the fall and some western mountain town like Park City in the winter and coastal South Florida in the spring.

[Omaharocks]

Originally Posted by SIGSEGV

Gets too hot in summer in Chicago, though it's fun. Maybe Anchorage would be a good respite?

That's a good point, Chicago does get hot in the summer, so isn't ideal from a temperature standpoint as a summer locale, probably somewhere like Vancouver would be best.

However, I've got family that are just a couple blocks from Lake Michigan in Milwaukee, and it's pretty amazing how much of an impact the lake makes in keeping things cool, even sometimes chilly during the middle of summer. I wonder if there is more of a lake effect/less of an urban heat island effect than in Chicago?

[SIGSEGV]

Originally Posted by Omaharocks

That's a good point, Chicago does get hot in the summer, so isn't ideal from a temperature standpoint as a summer locale, probably somewhere like Vancouver would be best.

However, I've got family that are just a couple blocks from Lake Michigan in Milwaukee, and it's pretty amazing how much of an impact the lake makes in keeping things cool, even sometimes chilly during the middle of summer. I wonder if there is more of a lake effect/less of an urban heat island effect than in Chicago?

Not sure, I don't live far from Lake Michigan either but I'm glad I have air conditioning...

[mr1138]

Originally Posted by Pedestrian

???? Chicago has periodic brutal summer heat waves and SF in winter can be as drippy as Seattle's reputation. It just depends whether the Pacific storm systems stay north or shift a little south and that seems to have to do with El Niño and all that stuff. Basically the California coastal rainy season runs from mid October to the end of April. Some years are quite dry (La Niña) and others are wet with rain as often as 3 days a week and not hard rain mostly--just gray and drippy. It's what I go to Arizona to escape.

This may be true, though I thought the point of this exercise was to choose cities we are actually interested in and not just a matter of choosing the ideal climate for each season. Tbh I had never really thought much about this until I read the OPs premise for the thread. But those are the two cities I think I would most be interested in living other than Denver.

I sure as hell wouldn't want to live in Chicago in the winter so it's gotta be my summer choice. I can deal with heat, though from my many visits to the city, my observation is that the lake tends to keep the temps at least a few degrees cooler than even its own suburbs (and generally much more pleasant than anywhere else in the Midwest except maybe WI and MN). As for rain in SF - I live in a place where it hardly ever rains at all so that doesn't sound so bad to me. I would take grey and rainy any day over icy roads and bitter cold temperatures all winter. If this were just about the weather I would definitely aim further south than SF, but there's also culture and urbanism to consider here. If my only choice is Arizona I'd say keep me in Colorado!

[twinpeaks]

Originally Posted by mr1138

This may be true, though I thought the point of this exercise was to choose cities we are actually interested in and not just a matter of choosing the ideal climate for each season. Tbh I had never really thought much about this until I read the OPs premise for the thread. But those are the two cities I think I would most be interested in living other than Denver.

I sure as hell wouldn't want to live in Chicago in the winter so it's gotta be my summer choice. I can deal with heat, though from my many visits to the city, my observation is that the lake tends to keep the temps at least a few degrees cooler than even its own suburbs (and generally much more pleasant than anywhere else in the Midwest except maybe WI and MN). As for rain in SF - I live in a place where it hardly ever rains at all so that doesn't sound so bad to me. I would take grey and rainy any day over icy roads and bitter cold temperatures all winter. If this were just about the weather I would definitely aim further south than SF, but there's also culture and urbanism to consider here. If my only choice is Arizona I'd say keep me in Colorado!

When it rains in SF, it's usually only for two days or so and then sunny most of the time in the winter months... actually, there's really no winter months.

[Shawn]

Originally Posted by Camelback

Your dream is to do sticky humid Boston in the summer? And chilly cool San Diego in the winter?

Gotta agree with this one.

Since it's my fantasy, I'll do this:

May - December: Southeast Massachusetts
- May through Labor Day: Martha's Vineyard
- Labor Day through New Year's: Boston
January - April: San Diego or New Orleans

For my current setup in Japan...

June - September: Ishigaki Island
October - May: Tokyo

[Crawford]

I know this is all fantasy, but this seems exceedingly impractical for most folks. If you have kids, they won't be able to attend school in the same location, their friendships will be truncated, and forget about any year-round activities.

And how many adults are 100% confident they and their partner(s) will work 100% remote forever?

For retired folks, yeah, this works.

[niwell]

I'm happy staying in Toronto for Spring and Summer, even with the seemingly increasingly frequent sticky heatwaves. We aren't buying anything here soon (if ever) though. My wife and I have been looking seriously at buying property in New Orleans, though we probably wouldn't spend more than a month at a time. That may end up more of a long term goal as we are also looking at small town Ontario / upstate New York for (winterized) cottage type properties with short-term rental opportunity.

In 2019 we spent winter in South Africa and it was very nice to be able to skip that season.

[MonkeyRonin]

My partner is from Vancouver and seems to be getting homesick. I like it out there too but would rather stay in Toronto. Realistically, it's probably not possible - 'cause these just happen to be the two of the world's most unaffordable housing markets - but ideally, I'd love to split our time between the two rather than have to choose just one.

So in the ideal scenario, we'd live & work (and let the kids go to school if we have 'em) in Toronto from September to June; and then relax in BC for July & August. Preferably somewhere on the coast or on one of the islands rather than the city though. I could do this for a couple months:



https://www.dezeen.com/2021/01/21/of...ar-clad-cabin/