While a student at UF, I started jumping with Falling Gators out of the Williston Airport.
There are ton of different sub-interests in skydiving. People who stick with the sport usually start going down some of these avenues.
One is a 4 person competition team called 4 way. There are all sorts of different formations. Organizers will draw these formations and you have to go through them in sequence. I was on the UF team. I traveled to Pittsburg for awhile and did a team there. Moved to Philly and I got on the dropzone team and we travelled the country promoting that dropzone.
Along the way, I ended jumping out just about anything that flew. Helicopters, biplanes, the back of DC9. Even jumped a hot air balloon out of Lake Wales.
I met Jeb, and he is correct. The more experienced you get, the more you need to push it. The parachutes get smaller and smaller as you learn. You get better and better at gliding them along the ground. The margin of error starts to decrease dramatically.
I dabbled in big way stuff. 20 planes would go up and 20 people would jump out of each. Highly, highly organized as to exactly where you need to be at all times. I really didnt like being surrounded by that many in the sky.
I started BASE jumping off the Perrine Bridge in Twin Falls, Idaho. 500ft. That shiit was nuts.
All that to say.... I tried a wing suit once. I had about 750 jumps at the time. An extreme noob in the elite world. Anyway, I knew it was "too far" for me and I only did it that one time.
One of my 4way teams leaving a Twin Otter (I am at 1 oclock):
Just as we are stepping off the hot air balloon:
Twin Falls (drogue chute used to deploy the main canopy is already in my right hand):