As far as small cuddys go, it' s relative what small means.
Go down to you local Grady White dealer and starting with the 20 ft Adventure, go in each cabin and see what works. Don't be concerned it's a new boat and the prices are what they are, you are only getting a feel for the size, no commitmenet to buy anything from dealer. Just say you are shopping. Dealers also broker used boats you can get on.
The Adventure (older ones had different names) is the most popular 20 ft walkaround and for rightful reasons, then going up in 2 ft increments they just get proportionally bigger. Bigger is better ride, bigger cabin, more fuel, heavier tow vehicle.
What tow vehicle you have is important, the boats get very heavy, even the Adventure should have dual axle trailer with brakes.
These models, up to and including the Islander are 8ft6in beam legally trailerable with no restrictions.
Each can be equipped with single motors as from factory, the Islander sometimes twins.
Then based on your budget and the boats you like, and what is too small and unacceptable ruling those out, start looking on boatraderonline.com, etc. to get a feel for model year vs. price in your region. But boats can be shipped anywhere these days.
Then get the the boat motor and boat inspected for it's condition, looks are always deceiving on structural boat issues. Motor is easier to figure out. For individual boat models you like, come back and ask here, plenty of owners for any of the models to help you fine tune the choice.
Good luck in your search.