You are talking about two completely different aircraft and completely different missions. I purchased a Supercub a couple of years ago. It's as practical as a Vespa on an interstate. On a fair weather day nothing beats flying with the door open and dropping into grass fields. You will enjoy the back country aspect of the Skywagon, but you need to understand it's limitations as well. If you are serious about going down that road, I'd recommend you figure out the tailwheel flying now. It is an absolute art and perishable skill, but if it's part of your foundational learning you will retain that skill longer. I honestly believe tailwheel pilots make better pilots overall. During my V1 cuts in the sim my nose doesn't move, I'm hyperfocused on runway centerline. You have to be with a tailwheel. Crosswinds will be a major concern and you will at least initially be limited in your runways with regard to crosswinds. My SC gets my attention about once every quarter, I get lazy and she will remind me that I'm not done flying until the brakes are set. Generally, just add power and go around and try again usually works out OK. '
You already know about Mooneys and tricycle gear airplanes. TW are a niche, while tricycles are mainstream. Depending on you mission, sounds like you enjoy travelling, a J will be hard to beat. You need to decide if you want distance, J, or weeds, TW. If you want the best of both worlds, buy a cheap Aeronca Champ or J3 and a J. After a year or two look back and see which one you flew more. Also, consider insurance. I have a friend who purchased a TW a few years ago and paid $10K just for that airplane. He had no TW time, but owns several airplanes and had several thousand hours. Good luck.