For some 12 or so years I transported mobile homes from 8' x 40' to as large as 16' wide and 85' long.
Be sure to provide adequate room when you turn as the trailer will cut the corner tighter than the tow vehicle.
As for backing into a spot, the longer the trailer, the slower the rear reacts to the turning of the tow vehicle. It's far more difficult to back a short 8' long trailer than a 85' one....... in my opinion.
Yes, wind can be an issue as the longer the towed unit, the more a side wind will push on it and move it from being 'in line' with the tow vehicle. When I was towing mobile homes, it was illegal to tow one when the wind was in excess of 25 miles per hour.
2012 Fun Finder XT 276 Toy Hauler & Harley Davidson Ultra Classic with Condor wheel chock
2014 Dodge Ram 2500 AT 4X4 Crew Cab 6.4 L Hemi, 373 gears, tow package, Rambox option, Revolver X2 tonneau cover, Equal-I-zer anti-sway hitch.