You are going to wonder why it took so long to switch to a 5th. Hope you have a 'modern' hitch. The old ones did not lock automatically when you locked in. That was the biggest reason for dropping the trailer onto the truck bed sides. Mine, I back under, the hitch locks on the kingpin and an indicator pops out of the front showing the kingpin is in place, the lever has set with the safety pin holes lined up. Is your hitch a double pivot? If not hooking and dropping your trailer can be a pain if the truck and trailer are at different slants. You may need to block your truck to the same level as your trailer to disconnect or connect. Just take your time, there is no hurry, don't forget to raise the landing gear or the rear stabilizers.
Biggest mistake is backing into your campsite, not watching your cab and ding the front of the trailer with the back of your cab. That usually takes a real sharp turn. I also have a short box so need to watch my angle when backing to hook up so my tail gate does not hit the trailer. Oh, last thing, don't forget to drop your tailgate! (don't even bother asking).
DRINK COFFEE--do stupid things faster and with more energy ! Rockwood 5th wheel, Signature Untralite, 8244S
Tow Vehicle: Ram 3500 6.4 litre Hemi.