Yes, we had a place in the North Carolina mountains for over 17 years; sold it this past October. I also have experience from two other viewpoints. My best friends had a condo in the Keys for many years, and we frequently discussed the issues you're raising and compared them to our cabin. Finally, when we were building the outdoor kitchens, about half of then were going into houses that people up North used as a getaway in Florida. I could see their issues, and they frequently raised them in conversation. I also owned a house in a gated community for about 8 years where my Mother lived until she passed.
So, having established my credentials, on to your concerns,
Security is going to depend on where you are. Obviously, rural areas with little crime will be safer than popular areas. The door to the basement in our cabin had a broken lock the entire 17 years we were there. I kept a lot of stuff down there, including a canoe and a motorcycle, and nothing was ever missing. Kids broke into the cabin twice in that period and took a TV, VCR and a rifle each time. But, the locks were so basic they probably used a credit card to open the door. Once I installed deadbolts, I had no further problems. Someone also walked off with a BBQ grill I left in the open on a deck for about 10 years. Considering that we used the place a total of maybe 60 to 70 days in the best years, that's not bad.
In an area like Florida, the condo is probably the most secure. However, the rules will grind you down. My friends eventually sold their place in the Keys because the condo assosociation passed restrictive rules about renters' boats that ruined his opportunities to rent the unit. He was a member of the condo association board but got outvoted by people without boats!
From what I've seen, the best place in Florida is a gated community. You will have little or no security issues. The least they have is a card-operated gate; the best have manned gatehouses and roving security patrols. Maintenance is no longer an issue; all the yards are trimmed and mowed by the maintenance staff, and things like repainting are done by the homeowners association. Facilities like a clubhouse, tennis courts, boat docks, often a golf course, etc. are available. The properties aren't cheap, and the monthly fees are significant, but it's the best all-around choice. Obviously, you want to examine the association rules and deed restrictions bery carefully before you buy. In my experience, the rules in these places are not changed as often or as capriciously as in a condo. The owners in a gated community tend to be more harmonious in their goals, while condos always have a type of parasite known as "condo nazis".
Both condos and gated communities will usually have an agent on site to handle the rental activities, and will often have maid staff to clean the place after a rental. There aren't many problems with renters in places like that, even with strangers; the rents are not exactly cheap and you seldom get riff-raff.
We went the other direction. When we rented (which was seldom and only to people we knew or who were referred), they were expected to leave the cabin the way they found it. We had a laundry room and they were expected to launder their linens and make up the beds on their last day, clean up the cabin, and replace and condiment which they emptied. In other words, go ahead and use the catsup, mustard, sugar, toilet paper, paper towels, etc., but if one of them runs out, replace that one item. Because they were all known and trusted renters, we never had to have someone check the place or come in to clean, etc. If there was a repair problem, they could call us, and we knew who to call.
Now, I know you travel to Florida frequently and have some ideas of the values, but I have to say that if you want an acre with a view of the water, you're even richer than I thought What you're describing, in the coastal area, would be very dear.
