In our case we started out tent camping. Then worked our way up to a conversion van, that I converted due to limited finances. We happily used it for years. The conversion finally died at 180,000 miles, and we focused on raising our family.
As we reached retirement age we decided to purchase a TT that we could be comfortable in.
FWIW It ended up being a 20 ft Aspen trail, that was luxurious compared to that van. Fully loaded weighes in at 6,600 lbs, towed it with a Chevy Silverado 1500 6 cylinder crew cab unit.
After 2 years, we ended up trading the truck in to purchase an 8 cylinder 5.3 liter engine with 8 speed tranny, and tow package, so that we could more easily handle the hills in Maine etc. We couldn't be happier with the combo.
I chose a 1/2 ton because I use it as my primary source of day to day transportation, and the trailer because it was easily towed with the truck, and the layout suited my wife and I perfectly.
The design is simple, reliable, (no slideouts) and at our age, the layout is easy to get around in.
It has a full size walk around queen bed, so we dont have to climb over each other or deal with the likes of a murphy bed every day.
With tandem axels it has a Cargo capacity of 3,400 lbs (with our current 2,000 lbs of cargo, we're near the max tongue weight for our truck}.
Take your time and look at all the factors that are important to you, and make your decision. ie: do you plan on going cross country, weekend trips, boondock for extended periods, full hook up,
how many people will use the TT, etc.
Safe travels and all the best.