My parking situation is very much analogous to my housing situation: I don't quite fit in. One of the most difficult parts of my situation, one that I underestimated during the planning process, is trying to fit the silly thing in parking lots.
Imagine this. It's Saturday morning, and you'd like to run some errands. No big deal right, just hop in the car and go do them. Think again. There are two ways your scenario can play out.
Scenario #1: You're going to the Mall
Sweet, we're going to the mall, a huge outdoor complex, parking should be a breeze, right? Still wrong. If it's even mildly busy, you're going to be constantly within inches of a multi-car insurance claim, and don't expect any other car on the road to understand that your vehicle doesn't maneuver as tightly as their Prius does. They'll pull right up to your front bumper as you're in the middle of a very tight right turn, and then look mortified as you play a game of Operation/horizontal Limbo that would make your childhood self envious. Not to mention the cases where backing up in the middle of a four way intersection becomes necessary. You've never seen fear until you've looked into a soccer mom's anxious eyes as you back your wrought iron tailgate nanometers away from her prized RAV4.
Scenario #2: You're not going to the Mall
So you're going to a small store, like a GNC or an Autozone. How do you know where to park when you get there? You don't fit in any old spot. If you're lucky, the spots might be a little longer than usual and you can back your tail end a few feet over the curb. That is if there aren't any poles, street lamps, or sprinklers, and if the curb is low enough that you don't bounce it off the gas tank. Otherwise, you have to hope that the lot is designed so that it butts two parking spots up against each other without any curbs, medians, or trees between them, because then you can just park and take up the entirety of two spots. Oh, and be on the lookout for low hanging branches while you're doing on this, or one of them might get caught in the sheathing on top of the box and rip the whole thing open. My strategy for not destroying my house has been to look up the area on Google Maps ahead of time, scope out a good location, and then hope nothing goes horribly wrong in the actual execution of the plan.
I did quite a bit of internal debating over whether or not the 16' box would be too cumbersome. In the end, I'm glad I have all of the extra space (compared to, say, a 10' box), but if you're even thinking of doing something similar, make sure you're completely comfortable maneuvering large vehicles. I drove 40' buses in college, and I never thought that knowledge would be so incredibly necessary for my future life as a software engineer. Life's funny that way.