Well, we'll see! Right now I am most eager to just get a trailer so we can ride for fun.
I did see that the club around here rides out of the very familiar state forest trailhead that is about 6 miles away ;~D
Downside of that is that these organized rides are a good way to discover ~new~ trails. :~D
Years ago I found a horse trailer sitting in a pasture - ugly black thing with dryrotted tires. I asked the owner how much he wanted for it and he sold it to me for $600.
I filled the tires with fixaflat type stuff and drug it home. We sanded it down, pulled out the rotted floor, repainted it to match the truck and put in new flooring. I sold it for $1200 years later when I got a divorce and had to give up all my horses.
If you're up for the elbow grease, you can reclaim one on the way to the junk yard (just about) for not much money.