Backing tips? Any advice before I hit something?

First video at about 3.48 his last get out and look before trailer actually enters the hole. Pay attention to the angle he has trailer at before entering hole.
This is key and providing your corner is over the glove as he uses you will not get close to the trailer on other side.

The difference your finding is in one of two things. Your set up not leaving enough room/time to achieve the angle or following the trailer in too soon.

 

The best way to learn is to back into your door in the Philly Produce market at 4am in a snow storm and you have to stick the trailer in between two customized large cars.

 

Or luck intona job shifting trailers on a UPS yard...where heavy-behind 53s come in with tandems all the way forward on the regular...which you're not allowed to adjust...and which just happen to be assigned to a door in between two other 53s...and 53s parked in the middle of the pad with barely 40 ft of space in front of you...

I echo what many say. Main thing: just take your time. Inch it in there if you have to. GOAL ten times if you have to. The main hangup will be that opposite (right rear) corner and making sure it doesn't scrape the trailer on your right side (if there is one there). Of course, it's a tidbit easier doing all that with a yard mule versus 200-something-inches of wheelbase on a conventional sleeper tractor, but it can be done. Just breathe, and take your time.

And if you find yourself getting frustrated, I offer this bit of counsel that I used to do in those tough spots: pull out the spot, circle the lot, breathe slowly a few times, and reset yourself. The worst thing you can do is fight yourself and a trailer into a spot in the heat of frustration.

 

best advice, take your time, never be in a rush

 

What about 2 or 3 pivot points?

 

That's when you go find the guys up in Canada and the PNW who pull B-trains and watch/study them for a while...and then ask 'em for pointers. I've seen more than a couple back B-trains like nothing...always did marvel at that.

*says the guy without a current doubles or triples endorsement...the closest I ever came to towing multiple conveyance was pulling baggage carts during my airline days as a ramp rat...

 

Just practice many many times and eventually you'll get a feel for it and it will come natural.

 

Y'all ain't wrong. It's time in the seat. Says the guy with no cdl.