I went from a 27' TT, to a 33' 5th wheel, now back in a 31' TT. Our son was small, and our first TT was just too small, so we got the 5th wheel. He has moved out, and it is just me and my wife. We went to a smaller TT, just for lighter weight, and not as tall. The 5th wheel was like 12' 6" to the top of the A/C. It was also heavy. I had a CC dually, with a Duramax, so no problems there. I just found that most 5th wheels are so big, that it limited me in a lot of campgrounds as to which sites I could use, be it from low tree limbs and such. The state campgrounds are known for never wanting to cut a single limb from a tree. I now have a 27RLS, with is just under 32', total length, and I feel that I won't have near the limitations getting to any campground I want. I will say that all of my trailers have pulled like a dream, but, I always had plenty of truck. I had a 2500HD gasser with the first TT, a CC dually diesel with the big 5th, and now, a 3500 CC SRW Ram CTD, that I pull the 27RLS with. The 5th wheel was very easy to hitch up. You won't have any problems with backing it and what not, it will just take some getting used to. Good luck with whatever you decide to get.
2016 Jayco 27rls
2015 Ram 3500 SRW CCLB Cummins/AISIN