Jupiter551 said:
Yeah, Oahu, Kauai, and the Big Island are all pretty awesome. Cost of living and employment are a concern. In the same vein, Key West is bad-ass...but not many jobs.
I went to Portland for a temp job that lasted 15 months. I liked the Portland area a lot. Very family-friendly, very eco-green, etc. Cost of living a tad high, but manageable. Other parts of Oregon might be worth a look. No sales tax in Oregon, either.
Lived in DC area for almost 2 years, and during that time, I traveled quite a bit up the Eastern Seaboard for work. No offense, but I can't recommend DC, NYC, NJ, Boston, etc. Not for me. Chicago is hit and miss for me. Cleveland and Detroit were mostly misses for me.
Currently, I live in a small, rural town in the Upper Mid-West. I'm sure that you could find a similar "small town" experience in most states. There are a lot of positives that I like. Crime is mostly non-existent. It is extremely cheap to live here (I paid my house off in 3 1/2 years, my yearly prop. taxes are $750). There are definite negatives. The residents are mostly friendly, but wary of outsiders. Even if they don't know your name, they'll know what you do and possibly make snap judgements. The "rural telegraph" runs 24x7. For years, I was treated like an alien, I was the weird guy who "did things with computers", or the weird guy "who worked on the internet" (yes, I have been stopped in the stores and asked that). A few years ago, my doctor's new nurse thought my insurance card was fake because she never heard of my company (IBM). Just recently, I feel some sort of acceptance. I'm beginning to be known as the "flower guy" or the "BBQ guy", which is a step up from the "weird guy"...lol! All and all, I can recommend living in a small town as long as you know the drawbacks.
Like you, I expect to relocate in the near future. If I have my choice (job dependent), it will be in the Texas Hill Country, around Austin (grew up near there). Otherwise, the sweet-spot for climate/cost of living, I would choose somewhere between Kentucky/Tennessee eastward to North/South Carolina. Where ever I end up, it will most likely be in a small town.
Good luck!