This is exactly why we got a truck camper! We fish bass tournaments as well as road trips to fish. I was concerned if this was something we could be happy doing, so I started out with a used pop up so I wouldn't have alot invested if we decided we couldn't do it. Honestly, we didn't use it as much at the tournaments as I wanted. But the trips we took..Alabama, Kentucky and state parks here in WV were great! We took it off the truck if it was for more than a couple nights so launching the boat was no problem.
The one trip we left it on...the putting the pop up up and down was a PITA, but the launching was a snap. BUT... my husband is a real pro at that backing thing.
We have an 18 foot Ranger AND a 22 foot pontoon...both have made trips with the TC. How about a back up camera??? Plus I am sure your wife would be a great spotter...put her to work.
Not only have I already made reservations to take it to some of our tournaments this year, but I am shopping around for a better pop up or a hard side. I figure if we didn't kill each other in a tiny one, a bigger one will seem like Heaven. Go to some dealers and just spend time in it with your wife. Move around in it like you would if you were staying in it. Get in the bed together! Pretend like you are cooking. We always take a canopy to put over the picnic table so meals are usually outside.
Hope this helps!