We currently have a 37.5 ft TT. We have towed it a lot of miles in the last 6 months. There have been a few tight parking lots, but most of the issues have been because I failed to plan ahead. I normally stop at truck stops with Fuel islands where the semi's fuel for easy access. On occasion we have had to stop at regular fueling stations. When that happens I just take my half out of the middle and block most of the pumps, I know it's a A-hole move but I grab fuel then move, less than 3 minutes total. The parks we have stayed at are not an issue, the longer trailer pulls and backs great plus it allows us a lot of living area with a 4 year old. I will say if I was going any longer than 38 I would seriously consider a fifth wheel, just to put 5-6 feet over your truck and help reduce your overall length.