Your question is all relative and depends on the individual -- I have a love hate relationship with winter and dont know how you do it in Wisconsin. We made the move 2 hours further north from Wichita KS to Topeka KS 3 years ago and just 2 hrs further North the weather and winter can be quite different. Topeka's humidity sucks - Wichita's was bad - but it is far worse in Topeka and like we live in a tropical jungle to me --- also the amount of Overcast and grey days - I hate it - Wichita had more days of sunshine. We NEVER went days on end without seeing the sun - that's been normal here off and on the past 3 years - thank the Lord we're hitting summer where that should stop until this fall hopefully.
Anyways - my personal preference is lots of sunshine and not days on end of clouds and grayness and hopefully no hurricane force winds for days on end - all things you can get in KS -
I've lived in
- Holcomb, KS - 9 miles from Garden City in western KS
- Wichita KS - most of my life with 1 place in city limits during adulthood, childhood out of town in a rural setting, and hs years on the edge of town in the burbs but with land
- Topeka, KS - going on 3 yrs now - we live out of town on land
- Ft Myers, FL during the height of the bubble and start of the crash in the 00's
- Cape Coral, FL - same time period
- Port Charlotte, FL - same time period
If we were to stay in KS - there are things I like about where we're at but we are not in "LOVE" with it - we're close to KC - close to downtown Lawrence and have a unique property that is affordable. We'd rather be living outside of Wichita - I'd also live in Dodge City, KS but my wife would never have it...ha - lots of open space, good people and away from all the rif-raf and easy access to the outdoor activities I like to do.
We've talked about New Mexico, Arizona, Nevada, Colorado and possibly Utah if we dont stay in Kansas. We dont want to get blown away by the wind - we've had enough of that in KS, lots of sunshine as alluded - the gray dreariness is for the birds - we get more of that in Topeka than we anticipated and lots of open spaces to be outdoors offroading, riding ATVs, fishing, pheasant or quail hunting, bike riding etc. If we're at least a couple hours from a major airport - that is another pre-req. We just want to live in an area where the government leaves you alone and you can feel safe going about your business with good neighbors. For me and I think my wife - the Great Plains and Desert SW can provide that.
I would winter in Florida - I did enjoy some of my time spent there - SW Coast would be where I'd go - Little Gasparilla is awesome, Marco Island, Sanibel etc - basically any place where you could have a house directly on the Gulf and there are walkable beaches.
I'd refuse to move my mixed race family to anywhere in the traditional "South" - ran into too many ignorant people over the years (Big cities not included - but as you can tell we're not big city people - we love traveling and exploring big cities - but no way we'd permanently live that life). Figured that was relevant given current events.