Neglected for medical reasons last year, and needing it, I decided to paint Larke myself this Spring. Nothing too complicated - one part Interlux paint - two coats of primer, three of finish. Lots and lots of sanding, mostly by hand on the small deck and the usual array of solvents, wipe-downs, epoxies, etc. The hull went well - roll and tip. The deck seemed to take forever, with weather, pollen and bugs not too cooperative. At any rate, she looks much better - but the ratio of maintenance to sailing this year will be something to think about.
Did the same with my decks, cabin house, cockpit spring 2017. I really wished that someone would do it for me but $$$ of course and never inquired. It took most of May but the boat was only 100' from the house. Brush & tip, looks OK for most part but well below professional standard (they would have wanted to remove hardware, too). I watched some roll & tip videos and was most impressed with two fellows in the Caribbean c. 1985 doing the same on topsides of a 50' or so boat while afloat, intensely concentrating.
Maintenance to sailing ratio is indeed worth a ponder!
I sympathize with you guys. Maintaining my rental properties is tough enough; maintaining a floating vessel can be a life-or-death proposition! So much depends on the strength of your rigging when tacking in a sudden squall, with rocks to leeward!
But in my sailing club here on Lake Michigan, we all do maintenance. And those poor boats are used every hour of the summer season. Ratio of maintenance time to sailing time per person is quite low. So maybe you're ready to sell the boat and join a club?