Went from an 18 foot TT, to a 31 foot TT, to a 35 foot TT. I find the 35 foot easier to handle than the 18 foot. Backing is easier and towing seems to be more stable (although tow vehicle has a lot to do with that too).
The longer the trailer, the wider you need to turn. I got very, very comfortable with the 31 foot, especially after 8 years owning it. I had no problem taking it anywhere, including gas stations, and this is towing with a long bed dully too.
Then this last Fall we got the 35 footer. It took a little learning curve. I avoided towns as much as possible for about 4 weeks until I got a really good feel for the turning radius. Once I "got it!" you know, the "AHHH HAAA!" moment, there's nothing to it now. Since then, I can maneuver it some of the tightest places now, been there, done that!
One thing you DO have to do when learning a new trailer ... TAKE YOUR TIME! If you think you can just jump in and drive like a wild rabbit, you'll be in trouble. Take your time, and let the rest of the world just suffer if you're inconveniencing them. At that point ... it's NOT about THEM! It's all about YOU!
You'll do fine! Enjoy, have fun!, and Good luck with many happy travels!