I'm new to all of this too - took my first trip this spring. Jayco with a Sidewinder - so I have little to compare to. I too have issues hitching up. To get the hitch to lock, you have to back in to the pin almost perfectly straight on. And that means straight on to the Sidewinder, not the trailer! Even two or three degrees off is asking for trouble. And if the sidewinder is angled right or left a bit, watch out for punching the trailer with your tailgate corner! My repair looks pretty good.....
Releasing also is a challenge, but one made easier by following directions. Read the manual about where to grease the pin. Mine came ungreased, and it was horrible - but after getting it lubed correctly, things got easier.
That said, I do like how it tows and backs very much. I'm sure it has already saved me from a crunched truck at least twice. And the weight/cost savings as opposed to a slider is a big plus.
So, as I get time, I'll play a bit with the adjustments and see if moving the wedge back a hair will alleviate the problems above.