I think its a great way to learn what your jeep can do along with meeting other jeep owners. I have been a trail guide with the program for several years. As for the trail most trips have different skills levels so you can find something that works for you. I would find a trip you think you might like and then look on youtube for video. That is a good way to get a better feel.
Also stock jeeps do great. Few things I would get if you don't have them. Front and rear tow points. Tools to unhook the front sway bar links and some zip ties to tie them to the frame. This will help your jeep flex better off road. Handles a bit like jello on road, so be ready for that. Other usefull items, CB, I also would say maybe some rockerguards if its in the budget, as to me its worth a few hundred to protect that area.