My dad has a 32' tilt deck that he uses to haul his bobcat. I've towed it several times pulling cars, trucks, bobcats, and pallates of rock. It's not that difficult at all to navigate, but part of that might be that I also have towed a 21' bayliner (23' trailer) and a 24' flat deck 4 wheeler trailer. To add to the complexity, my truck is a crew cab sliverado with a long bed... almost 20' long all by itself. The main thing with trailers is this: if you can't back them up very well, then you sure as hell better not pull into a place that you cant pull straight through. Otherwise your going to look like an ass. Just remember that a longer load is going to cut the corners a bit, so swing wide, drive slow, signal a lot, and people will be pretty forgiving to you. If you drive it like a sports car, your going to get into an accident. Just practice backing up in areas where there is little danger to your trailer or other cars... like a big parking lot or something. Pick a spot, and try to see if you can put the trailer in that spot perfectly.
I use to haul a 32 foot trailer around all the time for work and I think it was easier to navigate then my 10ft trailer esp. when it comes to backing it up because it will not swing around on you as fast as smaller ones.
We've got a 28' enclosed and it's not as bad as one might think it would be. We just try to avoid downtown and suburban areas as much as possible. Moving it around a gas station is usually not to stressful and backing it in and pulling out of parking areas at the races and unloading areas is rather easy as long as you don't try fitting it in too tight of a space.
In retrospect it's more than I need but its nice to have when you've got a few people along.