I have two tents with big vestibules (the Big Agnes Slater 3 could practically house a family of bears in the vestibule alone!). I notice that I leave my shoes/boots in the vestibule area and we cook under it if the weather is foul. Beyond that, we keep most stuff inside where it stays bug-free and dry. We haven't had any problem with gear inside bringing extra mess, we just keep the gear and such clean.

When hammock camping it's easiest to just stretch another hammock (my old Eno comes in handy) and put the gear under it so it stays dry. The tarp acts like a vestibule for the whole shebang.