I've only ever had one ride at a time, which is currently:
8.38 Resin-7 steep concave/kick
Ace 44 Classics
Spitfire F4 55mm 99
I love this setup but I'm always right on the verge of breaking it into like an 8.6 with my old Indy 149s (or even better, some new Ace 55s) and some 56mm wheels for bowls, and maybe an 8.25 with the Ace 44s for everything else. 8.38 feels juuust a little bulky to flip around easily, and I am also jealous of the dudes who fly around in the bowl with bigger wheels. But going up in wheel size to 56+ I will need risers and I feel like I might as well just go all in and do a bowl setup at that point.
With just the one ATV though, there is the advantage of never having to adjust to a different setup. I guess that's the only advantage....heck, you talked me into it, I'm gonna set up a bowl board!