congrats on the new rig!
When you are looking to back into a perpendicular driveway its easiest to watch the tires of the 5th wheel and guide then into the drive vs. the tail. By this I mean approach the driveway with it on your left (drivers side) then you can watch the tires of the 5th wheel as they angle towards the opening of the driveway, those tires are your pivot point. Unless you have a fixed object, then I like to have the inside tires on that side to pivot around.
When you start, have the truck relatively near the driveway on the cross street (so in the wrong lane) this will give you more room to swing the nose of your truck when you back in. But you only need enough room to swing the nose; so you don't have to be super tight to the driveway either (which will make it worse)
If you are having someone help you and that someone isn't used to guiding. Get both of you on a phone (put yours on speaker) and slowly and calmly talk through the process. If you aren't getting continuous 'keep coming' input stop and wait, it definitely isn't a race and by using a phone you aren't going to be yelling at each other over the noise of traffic, diesel rattle, etc.
I dunno why; but for some reason if my wife is helping, she interprets my loud enough to clear the noise of a Cummins voice as I'm yelling at her. Going to a phone fixed that :)
Practice; don't get rattled and take your time. You'll get better the more you do it.
