Yep. Totally agree on the balancing act between convenience of having a boat in a slip vs the time to rig
and de-rig a trailered boat. That's something I'll have to consider heavily.
I'm in the Newport News area - extreme southern Chesapeake. An appeal of a boat on a trailer would be launching on either side of the peninsula. When I had a power boat, it was very nice to be able to launch into the York River and cruise around that area, or launch into the James and cruise up toward the ghost fleet. There's lots of ramps around here. My current opinion is that a boat in a slip would limit our cruising area excessively.
But if rigging
the boat takes an hour on each end and is enough of a pain to keep me from going out, it doesn't matter how many places I "could" launch. That's why ease of rigging
is high on my list of features. Com-Pac seems to have a nice system; I haven't seen anyone else market their rigging
system like they do.