There are CGs out there that have TTs set up to rent. Easy way to test the waters and see what you do and don't like about TTs. That's what we did in the beginning. The one we rented had such a tiny bathroom you had to leave to the door open for a leg to poke out when sitting on the john. Bathroom layouts were high on our list when we shopped for our first TT!
Overnight not enough. Go for a 2 night trip at least and more is better still. If you rent an on-site TT in a CG, you won't have to worry about a WDH and setting it up right. First towing experience for many is white knuckle too and you could avoid that.
I'd also not put a lot of $$ into your first TT. After doing lots of research, we thought our first TT was a forever TT. Lasted only one season after finding it had too many shortcomings and was too small. Lost a lotta $$ when we sold it.
If you've never been RV-ing before, there's lots and lots of things you learn about them after you've got one. Some will be little annoyances like no place for a garbage container and having to hang a plastic bag off a stove knob to woefully inadequate storage space inside, tiny kitchen counter, nowhere to sit comfortably, etc.
I'd also recommend something with a slide out. And carefully watch actual tongue loads (not dry weight) of TTs vs. available payload capacity of what you're towing it with.