>>549365maintenance:
even the most prudent boat owners only paint bottom every 2 years, most do 3 years, if you're cheap and don't mind scrubbing it every week you can do 5
it takes multiple gallons to do it right, even on a smaller keel boat, and it's going to cost more than $100 a gallon, which is only the cost of the paint and not the haul/splash/yardfees/supplies/labor/beer
maintenance costs also vary GREATLY depending on your equipment. servicing your generator which powers your watermaker, ice maker, freezer, redundant nav systems with a 18 inch screen, autopilot, etc etc oh yeah and servicing all of those pieces of equipment... $$$$
or you could own a beat up cal 20 where every now and then you need to replace a line for $60
tl;dr the topic of "sailing" is far too general (what type of boat, what type of sailing, what type of sailor, etc etc) to say anything useful about maintenance, requirements, cost, # of crew, etc.