I always suggest for first-timers to go out with a seasoned Jeeper. They know the best trails and how to get out of sketchy situations. There is a ton of knowledge out there, so I loved your suggestion of getting involved in a club. After I bought my first Wrangler, I went out and joined the local club. They are a great group and I've learned so much!
Definitely something to think about. The one thing that keeps me from adventuring too hard is that I still have the stock radials. So I just do the 1-2 easy trails and even then I’ve only gone once. Eventually I’ll get better tires and wheels and I can venture a bit more
I learned a lot going with people that had been off-roading for a while. I actually became a very good spotter before I actually had my own rig and once I started rock crawling myself, that spotting experience helped tremendously