We went from a 20' to 29' TT (overall length). With the short TT I could drive up and down lanes in a Walmart parking lot. Now I have to park at the farthest corner of a lot away from other vehicles. Backing into sites is harder. We've just ordered a Garmin RV 760LMT GPS with backup camera that will help.
One thing that made a big difference was the wheelbase of the F250 we bought to tow the longer trailer. Used have a regular cab F150 and now have a super cab (and long box) that makes the wheelbase nearly 2' longer. Much more of a challenge to get around tighter corners. Even without the TT hooked up, the longer truck is harder to drive around town. But the longer wheelbase does help handling & sway. I'd recommend a longer wheelbase TV for a long TT and a 3/4 or 1 ton.
When I am backing up the longer trailer by myself into a CG site, I have to take it slow and get out and check often. When DW is with me, we have worked out hand signals that make backing up a lot easier.
I would imagine getting in and out of gas stations would be more of a challenge with a long TT and you could end up driving by a lot of them before finding one that will work. With a longer TT you'd want to take even more time and effort to make sure your WDH setup is optimized, tire pressure is correct, etc.
With a long TT, that's a lot of surface area to wash & wash... :(