Pop-up -> TT ?

considerations:
steel, wood or aluminum frames.
Siding material, some will delaminate easier than others.
roof construction - rubber, fiberglass, steel (cargo trailers only), aluminum.

All the above will get you a lot of opinions.

I would look at the all fiberglass "burrito" style trailers if you want less worries. The older ones had issues where the walls would sag and bow out over time and create issues, but Im betting the new ones fixed this with steel frames or something. Aluminum or steel frames for the trailer frame, steel is fine and durable, aluminum is lighter and will not rust.

The biggest thing for durability is keeping rain water out of the roof and walls and storing it in the shade or better, under cover.

Don't expect that longevity out of most of what is on the market today.

Rubber roofs need to be complete replaced, not just recoated, after about 10 years (unless you store it out of the sun).

1st step would be to look at the GVWR rating of trailer your interested in and make sure the intended tow vehicle can tow it comfortably and has payload to absorb the tounge weight.

That said, there are so many offerings from many different manufacturers in small packages.
R-pods even offer models with slides now.

Best thing would be walk in some models of interest.
Not going be much difference between manufacturers at a given price point.