After owning both, the only advantage of the 5'er over the TT is the stability when towing. However a smaller TT like WoodGlues Lance 1685 would be a dream to tow. With the 5'er you still need to drop the landing gear down before you raise the 5'er up. Not much different than having to using an elec tongue jack and lowering two stab jacks on a TT. The rear stabs on my 5'er are scissor type, same as a TT. Only difference is I have no WD spring bars to deal with, And I don't do a pull test. B&W Patriot:). Hitching up is way easier as I can see my pin and hitch. But then again installing a hitch up devise would eliminate that advantage. I know this for sure, it just seems physically easier to hitch and unhitch the 5'er. I would solo in my 28' 5'er before a TT any day. JMO though, as I like the towing stability. As an example we were heading south on 205 towards Frenchglen Or last week and the wind was blowing hard from the left side. All I could think about was the vvideo that been on here a few times of the guy with the dually and his TT flips over from high winds. I never felt sway at all but was worried some about the big sail behind me.
I do have a hard time backing in but attribute that more to the mirrors (Ram) than the 5'er/TT thing, as I towed the same TT with an F150 and our Ram and the clipon mirrors for the F150 just seemed to help more. The TT was 30'10" OAL and the 5'er is 27'10" OAL so they are pretty equal in that regards. If I were soloing and was serious I would go dually and a truck camper with slide out. That way I could haul a small fishing boat, cargo trailer or maybe an MC. Plus I could fit it in just about anywhere.