Yeah you definitely will. Mine is 19' (23'4'' OAL) and I am putting on a lift to get more clearance because it doesn't get into one of my hunting spots without dragging.

i wouldn't go too overboard on length unless you are planning to have several people in there or lots of kids or spending a great deal of time in it. I love my trailer but when I go camping my whole idea is to be outside. It's just nice to have a good mobile shelter with a lot more of the amenities.

as far as parking, mine fits most anywhere on per made campsites. Easy to back in and maneuver with. 23' trailer (~27' OAL) is all the more I would want to go or I would run into problems fitting it spaces.