Ramona said..
The problem with trailer sailers, especially large ones, is the launching and recovery off less than ideal ramps. There will be times when the wife will have to stand out in the water holding a large hull, often in a windy, exposed place with screaming kids while hubby wanders off for the car. There is a reason all those trailer sailers are sitting about in those storage facilities and appear for sale at surprisingly cheap prices.
Hang around a sailing club that sails trailer sailors and watch or give the blokes a hand to recover their Sonata 7's etc when the seabreeze gets up.
I would say you have pros and cons. In WA the pen fee is massive nothing less than $6k a year and it is not easy to find a mooring. Mooring are mostly in the river.
A hard stand, however cost, $ 700 at my club and there is no need for antifouling and bird shiiit cleaning before every sail. The boat is as safe as could be as the hard stand is fenced (electric fence).