Here would likely be my answers.
Hopefully, insurance mostly. But otherwise, we might each need to post to a damage fund.
It depends on the damage.
At least once weekly.
Uh, overnight anchoring out, daysailing, occasional long trip, and racing. At least 30 ft
Minimally—good sails, good & adequate ground tackle for 7:1 scope in 50 ft , VHF, depth finder, Windex, slab reefing set-up, hot water, two-speed sheeting winches, some type of auto-pilot
Generally, projects no bigger or more complex than swapping out batteries or alternators, or other types of simple replacements; rebedding stanchions &, bottom painting.
Above a neighborhood disgrace.
As needed.
Check battery connections.
Check fuel; bleed lines.
Find a fiberglass guy.
Take off the item, clean and prepare mounting surface, remount with some sealant such as 4200 or Life Caulk.