I for the life of me cannot get my head wrapped around this problem

It could be the line is not perfectly square to the dock.

 

He said in his original post that it is an odd habit he's developed. It sounds like he is doing that consistently. It's a pretty common tendency, even when the lines are straight.

 

More than once in a while. I banged many a dock running team with my brother. He's a master plumber and carries lots of tools and whatnot in the truck because he feels naked without it.

One thing he carries is a string for measuring 90° angles. It's actually pretty rare to have lines at a dock that are perfectly straight and perpendicular to the dock. He would often use the string and break out a can of florescent paint to mark the true line. Once that line is marked it's much easier to get straight to the dock.

 

That's funny I said that in another thread and some of then/posters said I would get in trouble for defacing property lol. Flourescent paint will be gone in a few days.

 

I will say I was very proud of myself backing into a dock during a blizzard in Massachusetts. Could barely see the dock and lines were under a foot of snow. Got er straight though!

 

By once in a while you mean 99.9 percent of docks don't ya?

 

I don't bump too many docks since I mostly do tanker but I'm ok at. Not a pro but decent. I hate blind backing with a van trailer, with a tanker it's not a big deal.

 

They construct buildings using lines, so it is just as likely the building is crooked, and the lines on the ground are straight.