I run a 2016 JK Rubicon, 2.5" lift on 33's, with some additional armor underneath. So a pretty mild build.
I have a few Badges:
Marble Head Loop - Drummond Island MI
Windrock Trail 16 - Oak Ridge TN
Windrock Trail 41 - Oak Ridge TN (an out and back to a place called Panther Rock)
SMORR Pee Wee's Crossing - Seymour MO
SMORR Guard Rail - Seymour MO
The Drummond Island and SMORR (Southern Missouri Off Road Ranch) were both Jeep Jamboree events, which offer a variety of difficulty levels within each event. The trails will be extensively pre-run, so branches, debris, etc will be cleared before the events. The trail difficulty will seem overrated, especially if you have some level of offroad experience on various terrain. The Jamborees, while expensive(ish), are a great way to get some offroad experience, as you have experienced, volunteer trail guides who are dedicated to getting you through. Additionally, they're big social events, and a lot of fun. Windrock Park is 77,000 acres, and the trails are maintained. There are extensive map options available, and the trail ratings the park provides are generally accurate. Pretty much something for everyone there.