Depending upon the orientation of the garage, traffic on the street, whether the driveway is straight or has a bend in it, what else you in your garage, and other things, it's possible that it could be easier to back the vehicle into the garage than pull straight in. There's also the chance that he has a wife that sometimes drives it and her backing skills are not that great and he would prefer to not have her add dents to the vehicle.Kata, curious, not challenging, why no room for the Top Lift Pro cost and availability notwithstanding? Does it tie into the idea that it works best as a space saver with a rig parked nose first in a garage and that you, as per the pictures, are a "back it in" kind of guy?
My driveway has a bend in it, so does my neighbors. I've never had a problem with it since having lived on a ranch, I have a lot of experience backing up vehicles and trailers, often into tight spaces. My neighbor though was somewhat "challenged" in that aspect and he had a nice scratch of paint on the corner of his house where he came just a bit too close while trying to back down his driveway one day. And, of course, his car had a matching scratch.
A lot of drivers just never trained much on driving in reverse. When I was teaching my daughter how to drive, one of the things that I did was make her drive in reverse in the local high school parking lot for extended periods of time so that she could be comfortable with it.