I have a small Coleman trailer I bought in 1976 and a restored 22' Airstream my youngest son and I use as a DJ booth for car shows.
With small trailers, it's very important to lubricate the wheel bearings once a year. If they freeze up when on the highway, you're in trouble.
Also, keep a spare. My Coleman has 10" wheels, so they're turning much faster than 16" car wheels.
A locking pin is important to prevent theft.
In many ways, a larger trailer is easier to navigate (back up)than a small one.
Of course, when you use a trailer, you have to pre-plan your trip to allow for more time in navigation, ample parking, etc.
Russ