Not being critical……
A thanks for each reply is really not necessary, just clutters up the thread.
Often see “Thanks to ALL that replied”.

Some Popular Hikes Near The Villages
 

Chinsegut Hill – Historic Manor House and nature trail to Lake Lindsey.

Sumter: Half Moon – Half Moon Wildlife Management Area.

Sumter: Lake Okahumpka – Lake Okahumpka Park.

Hernando: Cypress Lakes Preserve

Sumter: Hog Island

Hernando: Chinsegut Conservation Center – Beautiful Chinsegut - home of the red-headed woodpeckers.

Yes, I did kind of make that assumption. If a person can afford 2 homes then Florida starts to make more sense. But, with the global warming taking place, today Florida has HOT summers for about 5 or 6 months - not like summer in Buffalo, NY which would be for 3 or 4 months. The good things about the Villages are the MANY activities and they can be shared with people basically the same age (retired).
........I personally played some sports this morning (it was sweaty HOT, even my socks were wet) (my eyelids were sweating). But, now there is nothing to do outside so I am inside until about 7 pm when it cools enough to go outside and do some things in the yard. So, I am typing and warning you that The Villages is not All, La Land, and Rainbows. There are downsides. Many people have recommended renting for several months in different areas, that is good advice. I have just taken it a step further and recommended Crossville Tn (a retirement center near there). Also, a good combination would be The Villages for 6 months in the winter and 6 months in the summer in a place like Crossville, Tn or further north like Wi. With 2 homes, there are many good options. Just avoid Fl. in the summer.

The south has walking trails, that can be combined to become miles. Since they are around natural ponds, prairie, and weird wooded areas, views are always different. You take your cart to one of the parking areas, and take a walk.

You speak of hiking, are you looking for wilderness, or high climbing? There are great state parks within driving distance, but no real high altitude climbs. We tend to keep to the well groomed trails here, not a fan of the snakes, plus gators during mating season you will be amazed at how well traveled they are.

At our 3rd home in TV ( what used to be considered the middle) we have a pond across the street, that pelicans come in the winter, and fish out, staying for about a week, then move to next stocked pond. We have had panther, black bear, coyote, wander past our lanai cameras. We watch bald eagles and split tails soaring over our house.

We started in TV in 2007, and wondered every year what will come next, in 2023, it’s every month what is new. The charter school attracts families that come here to work, and get a great education in new state of the art HS. We tend to leave go to our northern lake home, cause this summer has been beyond any high temp Fl has ever seen.

Take time, it was four visits before we chose first vaca home, then continued to move to the next area we wanted to live. No attachment here to house, homes are relatively easy to sell, we have moving companies that will pack you and move your furniture.

There is a National Forest northeast of the Villages about a 45 min drive from the top end of the Villages where you could have about 100 sq miles of hiking. You would see lots of wildlife too. I have been there for hunting several years ago. It is tranquil and contains some SERIOUS Florida plants and animals in the wild.

Thanks for the comments jimjamuser.

Actually, I have been building up my own private list of pros and cons for The Villages for about a year. The issues that you mention have been on my list.

Also, I will emphasize that I wrote in my OP, "...am considering moving to The Villages..."

asianthree, you ask an excellent question about my walking/hiking preferences.

I think in terms of needs and wants.

My need is for non-concrete walking / hiking for 1-2 miles at a time.

My wants are for: walk / hike in nature; walk / hike that has a good amount of shade; walk / hike that involves climbing. I enjoy all of the above elements where I live now, but I am trying to be realistic wrt my criteria.

LaBelle is just a bit north of the center of TV right now. It's a nice (relatively new) area, close to golf, rec centers, squares, etc.

We first visited 4 years ago this coming Thanksgiving, staying with friends (who had moved off Moyer Loop in Pine Hills, 3 months earlier) for about a week. Just around the corner from LaBelle.

That was our "Lifestyle Visit". We were able to explore as much as possible, participating in as many activities as we could... Honestly, I was hooked, but the Boss wanted to rent for a bit to be sure.

So, a bit over a year later, we rented near our friends for two months. I traveled back and forth to work and the wife stayed in FL. When the weather was lousy, we went to open houses and went looking for new and resales with out friend's Villages Sales Agent (another friend had also used her and was also very happy with her). No pressure, showed us what we wanted to see after asking us a few questions.

She took us to see the new builds (only Chitty Chatty and Bradford we available at the time) and to see resales between 44 and 466A (as that seemed to be where we wanted to be).

There were some very nice homes for sale south of 44, but the Boss didn't like the views of the power lines, so Chitty Chatty and Bradford dropped off our list. We focused on the above mentioned ares. We found a nice Designer home in Oscola Hills at Soaring Eagle, a 3 BR 2 BA (that happened to be just down the street from another set of friends who had also moved to TV. We met them several years earlier before they moved to TV, thru the people we stayed with). Between all of them, we were able to experience much of what TV had to offer.

The price seemed right, we made an offer, came to an agreement, got a killer mortgage rate and settled in February 2021.

Luckily, we bought just before the "Covid Boom" hit, as prices skyrocketed a month or so after out offer was accepted...

We moved in in April and since then, we've been coming down as time allows. The Boss usually stays for 2+ months in the winter (I drive her down at the beginning for two weeks, fly back to work for 5-6 weeks, fly back to FL for another two weeks, then we drive back together in early March. She drove down in early June with our middle daughter and son in law, I flew down the last week of June and we drove back the weekend after the 4th of July. We'll probably do the same thing in October, then repeat the process until I retire (hopefully in 12-18 months)...

After living (albeit part time) in our home for 2.5 years, the Boss wants a 3rd BA (or at least another 1/2 BA), and I'd like a 4th BR and a pool (probably won't be able to talk her into both...). But once we sell the house outside of DC, we'll have a lot more cash to possibly make that move... As you can see, even in the short term, things can change!:D

And remember 2030 is a LOOONG time away and SOOO many things can change in that time.

ANY Realtor will sell you a property that may be out of compliance. It's impossible to check everyone's deed compliance before a sale. Especially since the different CDCs (I think they're now up to 14 of them) may have slightly different ones...)

Unless it's a glaring problem, you won't know unless someone complains about it (which most likely would have already occurred...)

If you are interested in hiking, attend the hiking clubs when you visit. Ask them when and where they hike, then you can plan accordingly.

Be careful when watching their videos. They are always cheerful and when questioned about wrong information they provided, their answer is always. "This is entertainment folks! Do your own research!" I find other YouTubers reporting on the Villages provide thorough, well-thought-out videos. Check out Rusty Nelson or Discovering the Villages with Jana Raber and a few others.

Style
 

*Really* like your style. Find your thoughtful replies anything but cluttering and appreciate your use of the equivalent of "bless your heart" for rather diplomatically straightening out misconceptions. :-) INTP comes to mind, if that means anything to anyone. . .

Had to google Labelle, but see that it's just about a mile to our east. Only been here a few months. Drove through a couple of times (relatives in Ocala), stopping and asking a few questions, before taking a couple of days on a long weekend trip up from SE FL to check out the real estate on our own. Put in an offer on the second day and have been most pleased with the decision.

Essentially all of the surprises, as compared to our "fantasies", have been of the pleasant variety. Have been a little surprised by how much can be heard from nearby lanais and bird cages, but mostly concerned about what they must be hearing out of my strange self. I speak to the video cameras set up for my lanai "driving range" (they make "sponge" balls that aren't loud and don't break stuff). Doesn't begin to compare, to me, to the "nearness of neighbors" issue in a condo on the beach in SE FL. Maybe it's just our particular street, but our neighbors are unbelievably friendly, as compared to anyplace else we've lived in recent decades.

If you can tolerate golf, "hiking" the "pitch and putts" didn't spoil any aspect of the walking experience for "us". Actually might even be missing said hikes since finally getting our golf cart. That also reminds me that a very high percentage of "good info" I've received here has come from the nice folks who sit behind the windows of the "starter's shacks". Good luck in your quest. You sound like the kind of guy who "enjoys the journey". :-)

mntlblok, thank you so much for the thoughtful and constructive reply!

You speculated that I am an INTP, and you were really close. Actually, I am an INTJ, and the 'J' helps explains why I am such an 'over-planner' (in the opinions of others).

Hiking a golf course would certainly work for me, and to be honest I had not thought of that since I wasn't sure if it was allowed.

Thanks again for your kind comments.

Randall, joining a hiking club is a great suggestion.

Actually, I belong to a hiking club where I'm living now, so I understand the benefits.

The purpose of this discussion, though, is to try to find locations in The Villages that are close to the type of hiking that I want.

Sharon, when you say that Villages Health does not accept Medicare, are you referring to both Original Medicare and Medicare Advantage programs?

My research indicates that Villages Health accepts a couple of Medicare Advantage programs, but not Original Medicare.

I would like to be corrected if my understanding is wrong.