I think your cynicism stands in your way here.
so you could travel through the stars, join star fleet, write a holo novel, explore the ruins of blah blah three, anything you want....and you choose to be a waiter
hmm, i think your gullability stands in yours
Yes, why not?
Besides, joining Starfleet isn't that easy.
Writing a holonovel... just because you can do it doesn't mean you're good at it, just look at the fan fiction section here.
So, to be cynical like you, even if you don't have to earn money, you can suck so much at everything else that the only thing that's left is being a waiter.