For the comfort of sleeping in a hammock, it took very little time at all, maybe a couple of trips. It took a bit longer to get my speed of setup and teardown right (especially since we almost always leave after work, so we Usually arrive after dark). I tend to sleep very cold (my body dumps heat very efficiently, which makes it difficult to keep warm in winter, even in Texas), so it took me a couple of years and lots of money invested before I finally got an underquilt setup I'm happy with -- the earlier options get kept in case I ever need to layer them. Pretty much the last thing I'm looking to upgrade will be to get a tarp with some doors, for when I go out under rain with shifting winds.
Gear storage? I'm not really a backpacker -- my wife and I mainly car camp at state parks, so if it's not something we're likely to need during the night, it goes back in the car.
As for playing games in the tent? We try to have a spare tarp to string up over the picnic table, or else, we're usually in a triangle of trees with our tarps overlayed to have an open area in the middle -- sorta double-porch mode. Plenty of space to sit and hang out.
"Can't we all just live in trees and hammocks?"
-- Sam Gribley, My Side of the Mountain