I went from pulling a 30' 5100lb surveyor sp295 to a 36' 8200lb surveyor s305 and actually found the longer to be easier to back! If you were comfortable pulling a trailer I can't see that an extra 5' will make much difference for you. Just take it a little slower til you acclimate to it. I'm glad we upgraded and have no regrets.
Steve and Michele Bassett
2014 Surveyor Select SV305
2005 Ford F250 Lariat SuperCab 6.0 TurboDiesel