I'd been a tent camper since I was a kid, and I know how to enjoy myself on a camping trip. As I got older, I graduated from tent camping to a pickup camper, then to a travel trailer. Shortly after I retired from the Navy, I bought a 34-foot motorhome, and hit the road. We spent more than a year traveling around 11 western states. It was great, relatively inexpensive (define "relatively"), and we saw a lot. I learned I don't mind living in a smaller space. I enjoyed the travel, and I was very comfortable. I could easily do it again.
What I learned I didn't like was the sometimes very crowded space in RV Parks, the cost of repairs and parts, and sometimes the unpleasant people who are living next door. The thing about an RV is the "getting there" is often better than the "being there." If you don't enjoy driving, if you aren't willing to do things for yourself, and if you're not a careful, observant driver, it can quickly become something you won't enjoy doing very much. If you don't enjoy doing it, you won't do it. There are a LOT of RVs for sale from people who thought they'd like it better than they actually did. There's a valid reason for that.
A teardrop camper is great, as long as it's nice weather. Do you ever plan to go where it rains, or gets cold? You may not have the space to get out of your own way. Great for a weekend away in good weather, but what if that doesn't work out?
A fifth wheel can be like towing a house. You need the right vehicle, and you must be prepared for the sheer volume of what you're driving, and towing. Nice place to stay, certainly, but even in the best of times, it's still "just" a trailer.
My best recommendation is to borrow or rent a trailer and/or a full-on RV in various sizes and configurations. Test them as if they were your own, and decide how much you like the idea. You may find that the romance of the idea is more than the reality of actually doing it.
Timesharing is what it is. It is very different than RVing, because you're moving into someone else's place for a week or whatever. With an RV or trailer, it's a lot like camping - you spend a fortune so you can live like you're homeless.
It's a fun way to go, but you have to know exactly what you're getting into. Good luck!
Dave