Small Boat Sailing
A trailer-sailor is a compromise boat. Whether it succeeds is a matter of finding the compromises that are correct for you. More people abandon the concept through traumas with the launch & recovery & the journey home than any aspect of the boat once on the water.
The launch & recovery operations must be achievable by one person using only whatever other facilities are regularly & reliably available. These other facilities may comprise of other people, a tractor, a crane or whatever. If you are always going to have them, then a large boat on an average trailer requiring complicated procedures will be a sustainable proposition. On the other hand, unless you can handle the operations on your own, the suggestion of going sailing will rapidly deteriorate from an opportunity to be grasped without further consideration to one that will be challenged & dismissed in a negative manner.