G'Day Shipp, and welcome to CF, the land of gratuitous advice!
I won't make a specific recommendation, but will relate personal experience: Many years ago, I wanted to take my self,wife and two small kids
sailing, doing much the same sort of things you describe. We were in the SF Bay
area, and had had a 16 ft day sailor dinghy
for 18 months, and had sailed the hell out of it.
We bought a recently introduced Catalina
# 61 (they eventually sold over 5000 of these boats). It was easily trailable, and we used it that way for about six months, but I found that the hassle of launch, mast
erection, sail bending etc was more than I wanted to do every weekend, so rented a berth in a marina. Kept that boat for 7 years, day sailing
, holiday cruising (Channel Islands, Monterrey, Canadian Gulf Islands, etc)... much the same program that you envision, and all in an inexpensive 22 foot boat.
My point is that a trailable gives you some options that are useful, saves you money
in an area where in-water storage
in winter is not done, and should be more readily salable when you want to move onward.
If you are like most of us, the sailing disease (addiction) gets worse with time, and your demands will likely increase. The size of your kids
certainly will, and more room and wider horizons will be attractive. They will probably be imperative! But with the modest investment of a 22-26 foot trailable, especially if purchased wisely and maintained well, you fiscal loss should be minimal, and leave you ready to move upward to a more capable boat.
At least, that's what happened to me...