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As others have pointed out, you're probably going to have to compromise. I'd suggest southern CA except for the cost and the shortage of green landscape. Along the coast of northern CA and farther to the north, you'd find the lack of extreme weather, but the climate overall is kind of cool to expect to swim outdoors during half the year. The Northeast and Midwest, and much of the western interior, have colder winters than you want. In most areas far enough south to have swimming weather anwhere close to half the year, it's likely to have either 100-plus heat with some frequency (AZ and TX, for example) or high humidity (most areas in the southeastern states).
Since you've said you may be able to accept some humidity, I'd suggest Raleigh as another city in the South. You might also want to consider the Hampton Roads area in Virginia (Norfolk, Virginia Beach, Newport News, and vicinity). If you find a place close enough to the coast, the summer heat and humidity may be tempered some by ocean breezes. Be aware, though, that anywhere east of the Mississippi is more humid than Colorado, and the South especially so. A place can be less humid than Florida and still be be quite humid. Also, in VA, NC, TN, or Atlanta, you're not likely to swim outdoors for six months out of the year, unless you're kind of hardy, but the swimming season will be significantly longer than it is in CO.
Hmm. Given your criteria, this will be a tough one. DC is lush and green, but very humid, and certainly not warm enough to swim outdoors 6 mo/yr (though you might get 4 mos). If you want the swimming and the green lush, I'd go with somewhere in the SE US, e.g. N. Carolina and points south.
I'd say Charlotte or Atlanta. Good weather, we (in Charlotte) have a pool and start swimming early May and go through end of September. Mountains 2-3 hours to the west, and the beach 3-4 hours to the east. Very little snow if any. The schools are moving in the right direction. You can grow pretty much anything, I have 3 palms in my backyard and they are growing great and a vegetable garden. Great banking industry, and so much more. An international airport. You can get a house inside the city limits for what you are looking for, although you'll pay for the location in taxes, my guess for a $300K house about $3500-5000 a year. You can get a house outside the limits and still have access to the city for less. Cabarrus, Union, Gaston Counties surround Mecklenburg (where Charlotte is). An even cheaper place is just across the border in South Carolina, Fort Mill. Our roads are a little behind, but Charlotte has grown so fast..... Good Luck. We moved here 10 years ago from Northern Virginia and LOVE IT. The worst thing is allergies - beware, they are really bad here. I had to go to 3 different stores to find Zytec-D. Look on the Charlotte page of this forum and see what others are writing. A few magazines picked Charlotte as the best place to relocate.
I thought of Florida... They have BEAUTIFUL state parks in which you have crystal clear springs 30 feet deep in which you can swim.
Manatee Springs sticks out in my mind, the water is said to be 70 degrees year round... I've been there twice, it is cool... It really is an attraction. I met someone from Houston while I was there... it is truly something I would visit yearly...
Miami sort of has a Major Airport... right? Or Jacksonville or Orlando?
The area is pretty Tropical, no so many mountains but there beach bike trails... and then you have the keys...
Home might be a tad bit on the expensive side... but good schools can be found in any state... you have to know where to look.
It does get quite humid, but not really over 100... usually 80s or 90s, sometimes 50s in the winter...
Humidity and Prices is the only factor that would worry me.
I would recommend Florida, Oregon, or Washington. People will recommend places in the south, but if Colorado is too conservative for you I'm sure Tennessee will be as well.
Seattle has a great job market, and is green all year. It is also extremely beautiful.
Portland is cheaper than Seattle, but the job market is not as good.
^
actually now that you mention it... Southern Texas along the coast might also work...
South-southwest Texas tends to be very liberal
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