OP - if you decide to rent, check out
rvshare.com. You can search for something in your area. If you decide to use it, let me know - have been tellng people about it and wonder if anyone ever uses it and what their experience was.
I have a 25 foot TT and backing up a 12 ft UHaul trailer is a lot harder than backing mine into a camping spot or beside my house. I personally would not be worried about going larger.
Not sure how big your family is, but realize how much time will be spent inside. Other things to consider is where you will keep it when not in use. Backing up gets easier with experience, although not that hard if you take it slow.
Sounds like you have a lot of childhood experience so now is the time to share that with your family. Good luck and keep the board informed!