Dang I'm a little behind, had to take a break because it was keeping me up all night. Thanks for all the replies!
So I'm getting this whittled down. When I take my State Tour in March my Sister will be watching my Dog. So if it goes well and she's willing to watch him again then I will plan a 3-6 month tour in NZ after I sell my house and put my stuff in storage. Possibly more trips if all is going well but I don't want to push it.
If it doesn't go well then hopefully by then I've figured out where I want to be and would rent a place or maybe spend a couple of months in each of these.
Las Vegas: Is sitting high on my list...reasons listed previously but mostly because it's a good jumping point and cheap airfare, no State tax.
Phoenix/Tucson: Tied for second, mostly because I'm familiar with it and I enjoyed it and already have Friends there.
Austin TX: I'd be close to Family, I already know people and it's a good City but I think I'd be happier if I was at one of the above Cities.
Overall I think all of these would be a good fit for me if I was married or didn't have much of the travel bug in me. Plus, I've been single (As in non-dating) for about 5 yrs and yes I have been putting myself out there but Wichita has slim pickens. I'm thinking a larger City would help me feel better about myself.
Erie/Fort Collins CO: Thinking it might get a little too cold for this sissy...but will check them out.
Greenville/Ashville SC/NC: I could be happy with these but a lot of the places I want to see are on the West side. I don't know when I'll get a chance to see this area but if I'm ever close I will check it out.
Maryland: I grew up in Southern MD and I have no plans on returning...got a mental block on that one!
Laramie, WY: This sounds like a great place if I was married.
Prescott/Flagstaff AZ: I think I would be happy at either but wondering if it might be better in Tucson/Phoenix since I'm single. Also, don't know if I'd like to drive the 2 hrs when I want to catch a flight.
Seattle: Seems a little too far from places I'd like to see but I'm sure it could open my eyes up to places I haven't thought of...like exploring Canada.
St. George UT: This is a great jumping point but maybe at a later point in life.
Salt lake City UT: Don't know enough about it, need to visit and read up more.
NorCal: Don't know enough about it, need to visit and read up more.
San Diego meets everything on your list except for the housing under $300K part, but you could find a decent rental for maybe $1200 a month.
DollarBill, I'll rent/sell you my extra house in San Diego for around those figures. Rent maybe even less. The area has all that's on your list except skiing would be about 1-1/2 to 2 hours drive north. Downtown is 10 min away and beaches 15 min. Lots of military bases. The house is on a hill with spectacular western views of downtown, the harbor, and the ocean. I abandoned the house and upgraded due to SO not liking the neighborhood. The catch? The neighborhood.
I've only been to SD once and I liked what little I saw. What's wrong about the neighborhood? PM me a link to it!