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Location: Gillette, WY, Layton, UT, Alameda, CA, Fairfield, CA, Fort Collins, CO, Denver, CO, Chandler, AZ
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You may need to look outside the metro areas a bit...for example: Phoenix, AZ may require moving towards Prescott, Cottonwood or Sedona where you are higher in altitude for cooler weather with four seasons, but not long drawn out seasons as Ill.
You may have to look at what is called a "rainshadow" area such the Front Range of Colorado, Reno, NV, or Bend, OR area. Still gets cold during winter, but probably half the winter as the Midwest with the humidity.
A more liberal area may require a city location to fall into one of these categories: large, resort, or college. A variety of Food and Music will fall into these categories as well.
IMHO, I would make an list of all the cities in different categories that suit your taste and then compare them to find matches. Then research.
Try Austin, Texas or Dallas (if you like big cities). Another choice could be San Antonio. Central and southern Texas weather may get below 50 degrees once in awhile, but it doesn't stay that way for long.
I live in Rockford Il, and absolutely hate it. Passionately! I moved here with my wife six months ago from Skokie (North suburb or Chicago), and we both have found life here an empty experience. We need more. Much more. On my end, I cannot stand winter any longer. I need more mild climates. I've been to Florida and Georgia, but didn't care for the humidity. I've been looking heavily into Phoenix (I have a friend there), but there is so much bad written about the sun city that I'm not sure. I considered Portland or Seattle, but the gloomy weather would be an issue (Depression, I get it bad during winter and too many rainy days (2 or more))
I think I'd prefer a more liberal city. I like movies, bookstores (used and new) a must. Continuing educational opportunities would be a consideration. Also, I have spent several years in an industry I have come to hate (Printing) and need some choices for a new career, something artistic perhaps as I do not do well in a corporate environment.
Basically, I liked alot of the choices in Chicago e.g. Food, music, shopping, fitness and so on.
I would like to offer up Albuquerque (or possibly Santa Fe) as a possibility to consider. Mild climate, great food, lots of fitness activities, and a growing city that offers a fairly diverse choice of occupational opportunities (including artistically based ones). Check out the 'New Mexico' forum for more detailed discussion!
I think Austin sounds like a near perfect match for you.
Weather-wise, Austin usually doesn't get below 50 degrees for a daytime high minus a few freak days. Summers are incredibly hot with temperatures usually in the 90s and oftentimes breaking 100 but it's not as scorching hot as Phoenix and Austin escapes the most brutal humidity of Eastern Texas a la Houston (although it's not so far West to have the dry heat of El Paso).
The city is pretty liberal and the University of Texas contributes a lot to the liberal ambience and the overall character of the city which in some respects is really an oversized college town. It has a wide variety of restaurants, bookstores, and is renowned as the live music capital of the country. The university and a handful of others in the area, also provide the opportunity of furthering one's education if you would choose to do so.
The economy is terrific with a low unemployment rate and a diverse economy in the IT industry, real estate, governmental jobs (since it is state capital), education, construction and the service industry. The cost of living here is also relatively cheap when compared to other urban areas.
The only drawbacks I can think of would be the weather (well, really just the summers) but that seems to be a trade-off you're willing to make, and also the incredibly high growth rate of the area means outside of the city proper, there's a lot of generic sprawl and some of the infrastructure is somewhat strained trying to keep up with the growth as is the case in most high-growth cities.
The biggest thing however is the fact that I haven't heard of a single person who spent time in Austin that didn't love it. Well, I haven't journeyed on over to the Texas boards to see what the locals are saying, but in general, people who live there seem to be very happy.
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