I consider myself relatively good at backing up with trailers. My neighbors have even asked me to back their rigs up into tight spaces. I have owned both TT's, and 5ers. Hands down 5ers are easier to back into tight spots, 5ers are also easier to line up to connect and can be hooked up at 90 degree angles (depending on clearance, sometimes even more).
There are advantages and disadvantages to both though. It really comes down to what you are willing to put up with. I currently have a TT, as I like to haul my snowmachine or ATV in the back of the TV. People have asked me why I haven't purchased toy hauler. One of my friends and partners in crime solved that for me with his toy hauler.... (a particularly bad road trip, spilled gasoline, made for a couple of smelly nights, followed by a particularly nasty muddy hunting trip convinced me not to purchase a toy hauler)
2015 White Hawk 25BHS Glacier Package
2004 Dodge Ram 2500, 5.7 Hemi, 5Spd Manual
2008 Arctic Cat M1000 SnoPro
Previous: Northface tent/Komfort 5er/Jamboree MH
Lance Cabover/Prowler TT/WildernessTT/Tiltin Hiltin Cabover/Starcraft popup