Harder ? Not at all ! Your truck & TT combo should work very well together ! Backing, and fuel stations will require a little more room, but nothing you can't handle!
Going with a TT will continue to allow for bed space for bikes, grills, wood, etc. and also allow for anything wet that you don't want to transport in the truck or TT !
No worries with the extra few feet ! Get out there and enjoy it !
I would continue with a good quality WDH !
2018 Forester 3011DS
2010 Flagstaff 26RLS (Sold)
2012 Ford F-150 Screw Ecoboost H/D 3.73
1930 CCC
Going where the weather suits my clothes !