I am struggling with the same issue (at age 65).
We live in Illinois close to Wisconsin. Great bike trails in WI and Mn and some decent ones in IL. Forget all that from November through March. It is really bad this year. However, these trails are so nice that we do not want to give them up year-round.
We found Inverness, Fl which has a great paved 46 mile trail and other trails close by. Also is a nice town.
Property taxes and insurance are NOT a great concern if we rent a house or condo. We studied the possibility of permanent residing in Fl and decided against it because of the high humidity (which requires an a/c buttoned up house, a no-no for me) and other factors which make the mid-west more attractive.
The cost of snow-birding is relatively affordable but has the downside of a less than perfect existence in FL. Life is a compromise.
I made a month long vacation in Inverness twice. Temperatures were 60-85 in mid-day but humidity was very high. Clothes would not get dry hanging outside. Mold would form if you do not do a/c.
Biking was great if you do not mind being wet from sweat and/or frequent rain. (I do not mind)