re: My job is 100% Remote Now; Where to live?

I hear Seattle is awesome these days.

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Easy answer. Earthroamer and tour the country

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This. I'd live and work out of a camper.

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You have my dream. You now are completely free to explore the world and live wherever you want. I am super jealous.

I am close in age to you and in a similar situation lifestyle wise (not career unfortunately.

What I would do is the AirBnB option for a year. I would pick 12 cities in different climates and live in each one for a month.

The ones I would pick:
New Orleans, LA
San Diego, CA
Portland, OR
Denver, CO
Nashville, TN
Chicago, IL
a beach town in Florida
Ashville, NC
Phoenix, AZ
Boston, MA
Washington, DC
New York, NY

I would also purposefully plan them around seasons that are either especially fun or especially challenging. That way you get exposed to living in a lot of different places and climates.

At the end of the 12 months, I would either pick my two favorites and decide to split time between the two cities or create a new list of cities to try and do another round.

Personally, I would imagine my favorites would be:
Chicago, New Orleans, Denver, and San Diego. I would pick the places I can most easily afford and rotate where I live based on the season. I’d spend spring festival season and football season in New Orleans. I’d spend summers in Chicago on the lake front or at Wrigley. Then I’d probably spend at least a month in Denver each year.

I’d just vacation in San Diego occasionally because it would probably be unaffordable.

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This is actually intriguing as hell. Idk about 12 cities in 12 months, might have to lower that number a bit for my preference, but this is a solid idea. How expensive would are AirBnbs typically for longer term stays? My rent right now is about $1100 a month for reference.

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Personally, if you're working remotely but want to be in a city, I would lean against NY. Not because it isn't awesome, because it is. But for what you can afford in terms of real estate, and keeping in mind that you have to live and work in that space, I think you're better off in a more affordable city.

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That's fair. I admittedly know nothing about the livability/affordability of living in NYC, other than rent is expensive in many parts. I would think $100,000 annually would be plenty to secure a decent place in Brooklyn, Queens, or the Bronx. And it's a city where a car isn't entirely necessary so you cut that insurance and parking expense.

I probably couldn't do it long term, but it would be awesome to do it for a year or so.

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Been looking a lot at Idaho, Montana, Wyoming, etc.

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Wtf

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Other cities I'm looking at include Miami, DC, and ATL.

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Miami son.

Depends on what you like to do in your spare time. If you like outdoor activities, Chattanooga, TN is hard to beat. The combination of activities available nearby and relatively low cost of living makes it very, very attractive. Plus, you would be within an 8 hour drive of an awful lot of the Eastern and Midwest US. Airport is small but super easy (and inexpensive) to get in and out of. More than makes up for usually having to make a connection to get to where you are going.

A lot of NYC landlords require gross income to be 40x rent. $100k salary will qualify for a $2500 apartment. There are lots of places available at that price point.

That’s corona pricing and/or the $7500 is based off of Christmas week.

$250/night is wayyyy cheaper than what it'd fetch during ski season since it's a 2/2 and ski-in/ski-out, so the dip is entirely made up of corona and length of stay.