Long overhang and dragging hitch delima--solutions request

I have a friend with a 40 ft Alfa Gold that is going to come up and try to back it in the drive. We will have lots of 2X8 blocking to use as helpers if needed. If that exercise goes well then I will put an offer on a 2006 Beaver Monterey that I have my eye on. I hope that is a good coach mechanically because it sure looks good inside and out. I just want to make sure I can get it up the drive first.