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If you don't mind some hot weather, I'd recommend Sacramento top of the list. Rainy winters, but nothing like Portland. The town is very pretty but mostly flat.
Forget Santa Monica, LA, San Diego, or coastal CA altogether. WAY too expensive. And you'd be surprised how chilly coastal CA can be, even in the summer.
I'd agree with Scottsdale, AZ too. Miserable hot, dry summers, but the rest of the year is delightful. Lots of art scene, street life, and educated people there. Low cost of living.
It should be noted that the Scottsdale summer lasts a good 7 months. Those few cooler months are golden though.
Denver is a paradox. It gets both plenty of sun AND snow. One of my best friends lives there and she is not an outdoorsy person at all, but she likes it there and there is plenty to do for her (she is 27). She owns a car that she uses to get out of town or around the city on the weekends, but she actually uses the train/light rail to get to work in downtown during the week.
Scottsdale...well you won't be worrying much about 'bums' there that's for sure. You can keep your car and enjoy a semblance of urban living due to the cultural amenities. In the summer you can plan escapes to Sedona and San Diego.
Santa Monica...fits your criteria in just about everything, except the shoebox statement. Micro apartments are, unfortunately, the current craze/trend there, so you won't be saving much money unless you get yourself a solid very well paying job. Thankfully, due to LA'S metro expansion, you always have the option for living in a great neighborhood like Culver city (with its own walkable main street filled with great restaurants, bars, art galleries etc), and taking the train into Santa Monica (the station is expected to open 2016.) Along with this, you have the renaissance downtown LA is experiencing, and the world class cultural institutions stationed there, like the Disney Concert Hall and The Broad. Just fyi, traffic is absurd in LA. Like nothing you have experienced in Portland. If you can go zen mode on traffic though, then you're all set.
Denver was the city that came to mind when reading the description, even before it was mentioned. I think this would be a great choice, as long as you are okay with some cold in the winter.
Scottsdale is interesting. It's pretty much a wealthy suburb. Sure, it's close to Phoenix and very nice, but it's not really a walkable, urban joint. And they have lots of strip malls (although very nice ones). Not sure that's the right environment, even though it's a very nice town. And I agree with the other poster that summer is long and incredibly hot. If you don't want to have to duck indoors for 4-5 months of the year, parking with screens on your windshield so you don't burn your legs getting back in the car, Scottsdale isn't for you.
Budget was not mentioned. Since you are on the west coast, San Diego may be a good choice.
Another interesting option for you would be Nashville. Thriving city, four distinct seasons but relatively mild winters. Great nightlife. Nice downtown area. Check it out.
-Sunny weather!
-Good fine arts & culture scene (ballet, symphony, museums)
-Nice restaurants & cocktail bars
-Good startup/tech community
-Walkable (especially if I can walk to work!) but I would still want to own a car
-Educated people
--Urban feel - not a strip mall/Walmart filled dump
-Nice new condos and apartments (why do people seem to hate this in a city?)
-Active and friendly people - tennis courts, jogging trails, yoga studios
A good alternative to the other places you mentioned would be Las Vegas or Scottsdale. I think Las Vegas checks all your boxes. It's very sunny to the point it gets half the rain Phoenix gets a year on average. Our culture scene has recently expanded with the Smith Center and we have endless entertainment options i.e. Cirque shows, concerts. Las Vegas has an incredible food scene compared to most of the country. If you move downtown which is gentrifying as we speak its walkable. Overall you need a car. Educated people....this isn't New York, Boston or Seattle, but there is a good mix here. New condos/apartments is where this place will really impress you, rents are downright cheap compared to So-Cal/PNW. People here are friendly overall and active is an understatement. Visit Red Rock Canyon 20 minutes from the strip and you will see what I'm talking about hiking, biking, rock climbing. We have water sports on Lake Mead and an incredible amount of gyms, yoga studios, pretty much anything you can think of. Las Vegas is more than the strip and worth checking out.
Gonna second this. Austin's nice, but you'd be trading dreary and damp for miserably hot and humid. What Portland calls a heat wave, Austin calls June, July, and August. The average high in Austin is 90 or above from late May until mid September. That kind of weather will beat you down, too.
The Hill Country is pretty, but it'll never be mistaken for real mountains. Those are a good 8-12 hour drive from Austin.
The Hill country starts right outside the western skirts of Austin, not 8-12 hours away!
-Sunny weather!
-Good fine arts & culture scene (ballet, symphony, museums)
-Nice restaurants & cocktail bars
-Good startup/tech community
-Walkable (especially if I can walk to work!) but I would still want to own a car
-Educated people
--Urban feel - not a strip mall/Walmart filled dump
-Nice new condos and apartments (why do people seem to hate this in a city?)
-Active and friendly people - tennis courts, jogging trails, yoga studios
Instantly Florida came to mind. I'm not sure about tech communities but everything else on your list screams Florida.
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