Just to clarify as I see I failed on this detail...my wife has a good paying IT/Marketing job that is full time remote ALSO having her real estate license as a hobby and to help us in building a real estate portfolio and with flipping houses... She is also heavily involved in our schools and community which she would continue wherever we land...Im not worried about her...Im the slightly under educated idiot that decided to work on cars instead of finishing engineering school

...Im going to have to retool/re educate a bit most likely and I'm aware of that hard truth. I'm 40, have a fair bit of college credit, 2 associates degrees and strong technical background...I can do alot of stuff and could finish a bachelor's in various different focuses in a short time.
I just have figure out what I really want to be/do when I grow up. Believe me, it's a bit of an inner battle I've been waging for awhile now and also part of what's pushing me towards this move.
I appreciate you input. We have been in the same semi rural, everyone knows everyone town for our whole lives, so I get the "Who the hell are these new people thing?"...and I'm sure it's an even stronger sentiment out there. Assimilation shouldn't be too much of a challenge though.
We do plan to take a trip out in the winter, like January/February once we narrow things down a touch more. I keep track of weather for most of the places we are considering. One thing we cannot take anymore is the humidity here. Hot/cold tolerance is not so much of an issue. Having just come back from high 90s in MT with low humidity to low to mid 80s with extremely high humidity...90-100 out there is more comfortable than 75-80 here...and I'll suffer the winters just for that.