Just giving away my 2 cents. My TT is listed as 35' maybe even 37' if you include the tongue. I used to pull it with a Ram 2500 before I recently got the current 3500. (Got the 3500 because I got a deal I couldn't pass and we hope to one day up grade to a big 5th wheel toy hauler and wanted the bigger truck and long bed, not because the 2500 was inadequate to pull our current TT)
If the TT has everything you need and want don't be scared of the length or let that keep you from being happy.
Our TT on occasion I will feel it porpoise (rock up and down) going down the highway or especially long bridges where the road segments are not smooth or have dips. But it never last long once the road smooths back out a little. I honestly think if I spent more time adjusting my equalizer WHD I could prob fix and improve my ride quality a lot. That said we have never pulled into the camp site and found the inside of the trailer trashed or things thrown around. We actually keep tons of **** on the counter and it's always right where we left it.
Just some back ground we have gone on a couple trips that were 1500 to 3000 miles each and several more trips to the Texas coast of about 500 miles each way and tons of local places around 100 miles from home (Only mention this to show my experience or lack of depending how you look at it)
Oh and I'll say this, as far as pulling with my new 3500 dually, only pulled about 150 or so miles with it, and it vs the 2500? Well first impressions, it wasn't like it was a night and day difference. Basically it seemed about the same. Biggest difference is my auto leveling air bags kicked in and I'm still trying to figure those out as far as what I think about them and the "alt trailer height" mode.