Nodding my head in agreement with Dutchmen Sport...wonderful advise!
We just bought our first TT in years after owning a 24 ft 5th wheel.
I would say that consider your needs: Are you going to be doing weekend or week trips? Are you just going to be parking a TT for the season or traveling to various places?
For a lot of traveling and weekend/week trips, a smaller TT would be suitable for your needs. But for extended stays, IMO, a longer TT would be worth it.
Also, if you can afford it, don't skimp on quality. It is the little extras that make a difference, like electric jacks, a solid frame, good flooring, etc.
The difference is price for a model the same size, is usually quality.
Furthermore, consider your tow vehicle. I don't care what the dealer says, a 150/1500 truck is not going to be pulling a 26' or more TT very well..there just isn't the umph on the highway.
Good luck with your search!
From the Adirondacks
Him-USAF, Ret. & Her-Landscape Photographer
Cougar by Keystone 5th Wheel
Silverado 2500 Diesel