I sail a Catalina 27. Sure it is "trailerable" but it would take a whompin big truck and an extra big trailer (empty boat is 6800 lbs). My 27 is not big enough to take 8 sailing, I had 5, including the wife and myself plus 2 adult nephews and a girlfriend, let me tell you, it was crowded. But that is me, your sailing may be different.
As for boats, there are a bundle of reasonable priced trailerable boats out there, Catalina 22 comes to mind first. Maybe you should consider a boat that can be trailered but stays in a slip durring the season. Setup and take down of even a modest sailboat is a chore for an afternoon of sailing.
Sailing on The Central Chesapeake Bay, West River, MD on my Catalina 27, Aelous II with my wife and friends.
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