You sound exactly like the wife & I, but I still do the driving.
1. An advantage to a midsize 5W is you drop it and have a vehicle to drive around. With the class C or A you will need a second vehicle for grocery's or site seeing.
2. The 5W will be more stable in winds than a travel trailer and you don't need weight distribution hitches. As long as the trucks large enough stability's not an issue..
3. You have one vehicle to maintain not two with the C or A.
4. Backing gets easier the more you do it BUT most places have pull trough sites so you don't have to back.
5. Over all length will be shorter, no tongue like a TT, no towing a second vehicle.
Recommendations: Diesel will have more pulling power than gas but will cost a little more in maintenance, up side resales better. Don't start with a small truck get a 3/4 ton or 1 ton prices are close and it will pull most 5W's. Unless your going with a really big 5W you don't need a duel rear wheel. I prefer a crew cab, I can haul groceries inside, my service dog rides in the back seat. I can take passengers, you'll meet people you want to do things with, go to dinner or such. While shopping for the RV you want to be able to get to the fridge, bathroom, and bedroom with it entirely closed. If you can you can make a sandwich, take a potty break in a wide spot or a nap in a rest area w/o having to open everything.
I'm retired LEO from WA so PM if you have any questions.