Depends on you
Hi Kyle,
It depends on where you are, and even more importantly, what your preferences are. I would say that the vast majority of my cruising friends in the northeast, who haul their boats out of the water for the winter, do not have their bottoms "professionally" cleaned for the entire season. They may brush the water line themselves, but do not hire divers or have the boat hauled during the season to clean. Assuming one has some kind of antifouling paint on the bottom, the slime and any hard growth comes right off with a pressure washer at the end of the season.
Now my (casual) racing friends, myself included, work a bit harder than that and dive or have a diver clean a couple of times during a 6 month sailing season.
I know more serious racers and they are also very serious about a clean bottom and I don't know how frequently they are hauling out / diving but more frequently than me!
Some other board members who sail year 'round can comment on their rituals, but I have seen some real corn fields growing on the bottom of some live aboards- seems like it would take a whole tank of fuel just to back out of the slip!
Cheers,