Not sure if you travel with pets...a mate/partner??
I used to like a trailer for myself.
Put Mrs G, a Rottweiler, three Shelties and a cat on board...and a motorhome was the only answer.
A trailer and pickup are no different than a motorhome. You have the same components. They all break.
That said, you already own what you own. If it works for you and you are comfy...why make waves?
What I find positive about my Class A...is pulling into a WalMart @ 2am and walking into the bed in pouring rain.
I am also able to tow a 30MPG station wagon on the trailer, instead of a 17MPG pickup being my only transportation.
Doing that math was the turning point.
We drive a heck of a lot more with the car than the RV.
Swap a 29 foot trailer for our 32 foot class A and it would mean a 3/4 ton truck.
This would mean every trip to the store, sight seeing...etc, would be about double the price.
Not to mention burning up big tires/drivetrain instead of the 4 cylinder Camry with common, low cost tires...ease of parking, ease for Mrs G to drive...etc.
We also have two vehicles that drive down the road. When the second fuel filter plugged up on the class A, I unloaded the car and chased one down.
Instead of sitting there, prey for road service overpriced BS, I had it fixed and running in less than 2 hours myself.
If I found myself suddenly single, I think I would put together something like the 17,000 mile diesel step van I currently have listed in the trading post.
That way, I could build out exactly what I wanted inside.
A leaky roof TT is easy for me to get a little help cannibalizing for tanks/appliances/goodies...and I would flat tow a small standard shift pickup truck or standard shift car.
Something that could get 30MPG.
Are you one of the guys who makes camp and stays there? Or do you take off every day and drive hundreds of miles on a whim?
Of course, you can buy a lot of fuel for $10K.
Your pickup or the Jeep could be flat-towed.
How many miles are you going to drive??? That is the real question.