I was doing the same upgrade as you except not as long. I read some good advice on this forum regarding backing the 5er. If you're backing line is wrong pull forward and correct to a better line. The fifth wheel reacts slower than a bumper pull and you won't be able to make corrections. Pull throughs are nice but you will have to back it sooner or later.
I was intimidated with the 5er at first and I jumped a couple of curbs but you get used to it pretty quick. I have to back mine into my driveway which is 90 degrees. Sometimes I do it right and most of the times I fail on my first or even second try. There are some good youtube videos regarding backing strategies.
Congratulations on your future gear.
