I am not sure if one ever gets use to the cold, I was born & raised here, lived in MN. for 13 yrs. but colder here, the only thing that has really changed over the years is we do not get the snow like we use to.
I spent 4 mos. on GA. 2yrs. ago that took some getting use to (Heat & Humidity) but I'd take the heat anytime over the cold.
I drive truck also, deliver new trucks all over the U.S. and Canada and have been to every state encluding Alaska and I would pick TN. to live I think that state has it all, kinda like WI. except for the weather.
I almost took my camper to MS. for the winter, but hard to find someone to look after the critters that you can trust, so I'll wait a couple more years and should only have the horses left to move, my last 2 dogs & wolf are all 13 yrs. old and won't be with me much longer, sad to say.
I'd keep my farm here (paid for) and look for 20-40 acres there, that way I'd have the best of both places when I retire, maybe in the next 3 yrs. all depends on the health, I should have retired in 2011 but as long as I can work what the heck.