I definitely agree, Pax, that being half of a couple makes decisions on where to live harder! During our 31 years of marriage, we have moved quite a few times, and in most cases,, one of us was ever so slightly more gung-ho than the the other. And every lifestyle change/decision has been like that. Obviously we would never make these kinds of decisions unilaterally, but one person has to compromise his or her ideal choice more, perhaps.
If I were single, I am quite sure I would still be living in NC, not nomadic at all. I would not be brave enough to live this kind of lifestyle alone, plus I'd get too lonely if I didn't have a partner, since I'm introverted, so making new friends can be tough. With my DH, I always have one built-in bestie!
So, I am grateful to him because I think of how much I would have missed out on, so many amazing places and experiences, if he hadn't been driving these changes. Maybe your wife feels that way, Pax, and maybe she'll do just fine. As I mentioned in a previous post, when we moved to Florida, briefly, years ago, I loved it too, but I quickly adapted to life back in NC when we returned. And I was happy there too. I wish the same for your wife. But that doesn't mean that I don't feel your dilemma.
BTW, our healthcare is through the Obamacare exchanges in Florida, and we've found it to be fine for us. We have a low-cost Florida Blue plan as we're both too young for Medicare. But we didn't have the choice of a better plan in NC as neither of us qualified for a retiree medical plan (we worked for the same private company for years, and they finally declared bankruptcy), If we'd had something like you describe in IL, leaving would have been much more difficult, and we probably would never have done it.
I wish you peace with your decision, whatever it is.
Emily
2011 Jamis Dakar XC "Toto" - Selle Italia Ldy Gel Flow
2007 Trek Pilot 5.0 WSD "Gloria" - Selle Italia Diva Gel Flow
2004 Bike Friday Petite Pocket Crusoe - Selle Italia Diva Gel Flow