I think I remember you made a custom overhead bunk for your daughter ?
After owning both types, its a personal choice dictated by your style, needs and family size .
You will miss having the tc with you all the time if you left the camper on the truck all the time. You might be able to offset that by towing with a van.
Having the trailer offers more room, an easier bed to get into, a shorter climb in/out of the camper/TT and lots more storage.
The size of the battery trays sometimes only allows smaller batteries. If you boondock, you might need to alter the battery tray.
Towing has to made level. The weight has to be distributed equal over both axles on a trailer. Make sure your hitch head set up is done correctly. There are adjustments with setting up the hitch properly. Have enough tongue weight to limit sway and do not place too much weight on the TT rear axle, make it equal. This all affects the tow, axle stress and trailer tire wear.
Backing up a trailer is no harder than putting a camper under a truck...practice it . While backing up .... Place your hand at the bottom of the steering wheel , if you want the rear of the trailer to go right , make your hand go to the right. Its also easier to back in on the drivers side, you will lose your mirror view on the passenger side. A spotter with a handheld 2 way radio will help .
Im pretty good on backing one into tight places and I have seen people back TT's into places where you would think they would never fit.
If you pick the right TT floor plan , you could get a 1500 truck with no mods or special equipment to do the job.
With a TT you have options. You could plan to lease a new truck every 3 yrs. and always be covered by a bumper to bumper warranty with no expense of modding it up.
You could also use a van to tow with. Passenger space for a family with storage. Some people have them for a porta potty option . The windows can be screened and fantastic fans added to ventilate ,( if you have a pet to leave in it while parked ). It could also be used as a solo camping unit if you like to go alone on fishing trips etc .
Good luck with your choice , research trailer tires.
Bob