The trailer traded for was older than the trailer the boat came with: A "Sport Trail". It was a premium trailer, and I put E/H brakes on it, (another $1000). The VIN was missing. I called the owner of the builder and he looked up the trailer and sent me a new VIN sticker with the proper numbers.
There are so many things that would make a C Dory better. For example I feel that for those who cruise should have a camper back with both screens and rain occlusive windows is essential. There are just no two which will be fully the same.
If I were doing the trailering back and forth cross country, I would definitely want the tandem axle trailer and pay for it. If I were only going a few hundred miles or less a year, the single would be fine, with brakes. Any trailer over 3000 lbs should have brakes--and are mandated are to have brakes (and many states, like Florida, require brakes on each axle.). My understanding is that you have to comply with the local law ref brakes. Calif. and NV require brakes on any load over 1500 lbs. I would probably upgrade the tires.
There used to be some rational, like age, accessories etc which determined the selling price of used C Dorys, esp the 22. Now there are some crazy numbers, but a new boat sells for crazy numbers also!! And it will go up with inflation, higher petroleum costs etc.