I docked a 19' Renken in Lindenhurst and Amityville from 1978 to 1986 and have been trailering a SeaPro 180DC (of course, I can see the boat ramp from my driveway) from 1999 to now. Had gas siphoned, battery sabotaged, and safety equipment swiped at the marinas, and would NEVER leave fishing equipment or any electronics at the marina or on the private canal in Amityville. Trailering- ONLY gripe is I have to jockey cars a little bit more in the driveway again, and I can't keep a killie trap over the side. (virtually stopped using them, but I can keep them alive in the shade outside my garage with brackish water and an air pump for over a week anyway) No bottom painting, Mr. Mossberg for home security, easy access if I want to repair or measure for modifications, no walking through someone's backyard during their kid's party, and no competition at a marina for hose, electric parking. Plus the gear is in my locked garage, 9 feet from the boat. Boat ramp's got a washdown area as well.
My own waterfront home would be the dream, but only Lotto would make that a reality. Haven't even greased the bearings in a year, but for me, 40 or 50 outings only equals 50 or 60 trailered miles. As usual, to each his own.