Anaro - We hauled a TT for 2 seasons, and then upgraded to the 5ver in signature.....on the way home from the dealer (100 mile trip), my first time hauling a 5ver, and going around the Wash DC beltway - all I could do was grin and giggle - I could not believe how much nicer it was to tow than my TT.
I also no longer have greasy banged up shins....and that's really nice. Go for the 5th wheel.
You can always have your co-pilot get out and check for branches...if you think they might be close....my DW has no problem doing that for us.
Good Luck.