I have never been more than a Private Pilot after starting out hang gliding, moving onto ultralight aircraft and then GA aircraft. My brother and I used to construct huge Rogallo style kites that we would try to get pull each other aloft behind our tractor. Later after he was already flying for a regional airline, I bought an old Rogallo style hang glider that had floats and we towed it behind his boat. It was a lot of fun, but not really comparable to flying in the mountains under a double surface high performance hang glider wing.
I have enjoyed playing with flight simulators for many years. Although this has been somewhat sporadic depending on what else I have had going on in my life.
Here are a few more examples of "auspicious" Flightsim users who made a mark or two with their extraordinary/unusual skills.