It sounds funny to say, but no amount of money or freedom from any obligations would convince me to live anywhere else other than where I am now (CO, between Denver and Boulder). Some reasons why I love it:
1. Lots o sun
2. See # 1 above
3. Beautiful, quiet trails within walking, running, or biking distance
4. Great community - for me the right mix of respecting differences and privacy while being genuinely friendly and rallying together/providing support to others in times of need
5. Four seasons, with winter being entirely manageable because we get nice fluffy snow that melts quickly
6. Easy access to major city (Denver) and small city (Boulder) whenever desired
7. Blue, but not hyper partisan or progressive
8. Low humidity means no mosquitos or mold, both of which I had to deal with in past places I've lived
No place is perfect though, and we definitely have drawbacks:
1. Biggest is lack of water (scenery can be brownish, no big bodies of water for swimming, and may portend arid post-apocalyptic warzone in near future)
2. We may officially be HCOL now
3. Sometimes a little humidity is nice, esp. in the winter, when if you're not careful your hands will crack wide open from dryness
Now if the question is where would I want to have a money-is-no-object place as a second home, then that would be somewhere in the LA/OC/Carlsbad area. Love SoCal too.