Uh, ahem, I did have a problem once just after we upgraded from 20' to 29'. Found the last site on Wa. coast next to the water but it was very tight. Backed partway in, unhooked & repositioned the truck, then backed all the way in. Fantastic view, mere feet to the beach and worth the extra work to get in. On the way out it *looked* like I could just drive out without unhooking partway out. Wrong. Ended up getting the TT stuck between a tree at the front and another at the rear with literally only an inch clearance at each end. :R CG had to bring their backhoe over to pull us sideways to get out. I'd post a photo but can't because of what PB has done and am not at home. Never do what I did, no matter how good the view is... :(
Anyway, I think you will find that the only thing a longer TT will affect you to any degree is strong gusting side winds and then all you can do is slow waay down. Don't expect a WDH to overcome that type of wind.
You def. have an excellent truck to tow a longer/heavier TT. JMO, I'd suggest some HD shocks on the truck and if you can, shocks on the TT. Good choice on a Jayco as that model has a BAL frame.
