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To iceTr0n: can you visit Portland for a week or two on vacation? You could check out the employment situation while you visit, but also have a nice time in a really nice city.
On staying put: consider finding a cause you believe in, which needs volunteers. Helping a cause or assisting others directly will help you feel less trapped. You might meet more people than you normally do, as well.
Perhaps an annual visit to Portland or another place would function as a tonic. Maybe a winter trip to the Gulf area, or Hawaii would be good for your mental health.
Many times our personal circumstances make use feel trapped and hopeless. We've wanted to move for a long time, but we couldn't sell our house. Now we are finally moving. My point is I understand how that feeling is. We had to make the decision to live in the moment while planning for the future during our years long wait. I hope you can find a new path for yourself.
You can keep on the same path, but change will require you to change, most likely. Good luck!
I was in Portland last July. It was unseasonably cool, and overall it was lovely.
If you can, drive to the coast. Cannon Beach is good. The Oregon Coast is sublime. Can't swim there because the water is too cold, but sitting in the sand on a sunny day is wonderful.
And on another day, drive down the Columbia Highway and hike up to some waterfalls.
Take a Fruit Loops tour around Hood River and buy some fresh cherries. Have a meal at the hotel in town.
And for your cold Montana winters, visit the Pendleton outlet in Washougal, WA for a deal on a warm wool shirt.
Location: Temporarily in Niagara Falls, Ont. Canada
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Although I've never been there, I've heard Asheville, NC is a really cool place. If you were considering Portland, OR you might like Asheville NC, even though it's on the east coast. Might be worth taking a look and making an exception. I'm like you in a lot of ways and seriously considered Asheville if I were to live on the east coast. Although if you're hoping not to see any mountains anymore, Asheville may not be the right place for you. But I hear the weather is a lot nicer and so is the vibe.
Asheville is beautiful. I gather the work situation there is very difficult and it's become "a place to be" so housing has gotten quite expensive. Lots of cultural stuff, and nice mountains, decent weather. Maybe getting as crunchy granola as Portland but with more pleasant winters.
Have you considered Boise? Weather-wise, it seems similar to what you're probably used to. It's bigger than where you're currently from, but not too big. And it seems that the types of local industries would be in need of your IT skills.
I just re-read OP's full post and wonder, could he find people online (I don't mean dating, I mean gaming, etc.) to talk to and ask them where a good place to move would be, involving tech and gaming?
Also, I recently talked to a friend in Portland. She has long complained about the weather nine months of the year- raw, grey, raining. I didn't think 40s-50s is so cold until you factor in the grey windy rain. She says it's like that nine months of the year, and then the summer months are like paradise, nothing prettier. OP mentioned wanting more sun than Montana and I think he might be misled visiting in July and September and all. Most people suggest if you're going to move somewhere based partly on weather, go in the worst season and see how it seems.
I really think online gamer people and techies might live in all sorts of places, enclaves, that OP hasn't thought of yet. If I were him, that's what I'd do.
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Portland in July is good
