Nah, I've already thought it through. I'm jumping a rental Sabre 170 right now. I'm a small guy, so that's almost exactly a 1 to 1 wing loading. I'm pretty comfortable with it. I feel like it gives me plenty of performance, too.
I figure by the time I buy gear, I'll maybe want to go to a 150 canopy. That puts me at a 1.1 wing loading. That's all the further I care to go. I fly enough high performance airplanes during my day job. I'm not interested in zipping around under some tiny little canopy for fun on the weekends. I live a really calm life...no motorcyles, no skateboards, no skis or snowboards, no rock climbing...skydiving is the most "extreme" thing I do, and I try to keep it as mundane as possible. I just want a canopy that will be easy to fly, glide fast enough to penetrate these crazy Nebraska winds, and get me on the ground in one piece. I leave the swooping and downwind landings to the guys who are younger and dumber
As for free flying...I might try it a little, but belly flying is what I'm more interested in. I want to get good enough that I can fly along with the 8+ ways at boogies and such. It looks like a ton of fun, trying to turn points with that many jumpers. I think it's all a function of who I hang out with, too. Most of the regulars at my DZ are belly fliers and nobody really talks much about free flying.
But who knows...I have a lifetime full of jumping ahead of me!