I would think hard towards changing the approach angle of the drive--have a problem with maybe putting too much leverage on the frame between the hitch and the roller.
From your description, you might actually end up with the trailer wheels off the pavement for a short interval, with all the weight of the trailer on the hitch and the roller.
Maybe you could measure the most extreme lift between the drive and the street with a line and see how much the trailer wheels would drop at that point.
Also, with a 43' unit, and having the roller/casters hanging down, it might restrict getting backed into some camping sites that have a concrete stop at the rear--we routinely have to back our 38' Suites over those type stops to fit in some state/forest campgrounds.
Sounds like a nice unit, hope you can get it worked out.
'05 36TK3 Mobile Suites
'10 F450 new to me
'09 F450 Lariat 4x4--died