Not to worry, I respect/appreciate what Jeff_H has to say. As I''ve mentioned elsewhere, we do have somewhat different ''philosophies'' but his experience on various types sailboats is definately helpful and his analytical approach enlightening.
I also fully appreciate what it costs/takes to maintain a boat as well. I was once a licensed Coast Guard captain (on a 43'' stinkpot) and completely restored a Rhodes 19 (including installing mahogany toerails, new keel frames/bolts, duckboards, deck/hull paint and even some nice, decorative marlingspike

etc.. Sailed her offshore up/down the coast and enjoyed every minute of it which is what planted the seed I''m watering today.
I don''t think $3K/yr is an outrageous sum to consider for maintenance. It certainly wouldn''t hurt to ''earmark'' some such sum just in case. But I also think the annual maintenance cost will depend on the choice of boat and the onboard systems.
Fortunately (as I''ve mentioned elsewhere as well) I''m a backpacker, not a ''RV camper'' and certainly not trying to replicate my shore life comforts on a boat (I just inherited some $$$, I didn''t win the lotto

. By & large the most complicated systems onboard will be diesel, propane, windvane, solar and the fresh/saltwater plumbing (galley/head/bilge). As a possible compromise to my shore comfort I will consider refrigeration (although I''m leaning away from it). Only electronics will be VHF, CW/SSB (I''m a licensed ham), a hand held GPS and a simple depthfinder. In short, I definately plan to K.I.S.S.. No digital pilots, chartplotters, radar, A/C, watermaker, hot water heater, etc. wanted/needed.
I''ve also got the skills to do pretty much all my own maintenance (with the exception of diesel mechanics which I''ll learn). I''ve got good fiberglass, electrical/electronic, wood & metal working skills.
Finally, I have no intention of buying a boat that will take a year to (re)outfit. Whatever boat I buy will have a sound hull, fresh sails, rigging, etc.. and configured for shorthanded sailing. If it doesn''t, well, I''ve waited years to get here, I can wait more if needed to find the right boat for me. This is not to say I think I''ll be able to find a boat I can just step on and sail away. No boat is perfect. Just I''m not going to buy a boat that needs the deck replaced or new standing rigging and/or change the windvane because I just have to have an Aries.
Bottom line is, I know what it takes to maintain a boat (never let it get ahead of you) and short of a freak catastrophe or doing something stupid (always a possibility

can manage any maintenance costs to be in an acceptable range.
But I hear you. I distinctly remember, back when I was a ''professional boat driver'' how when the boat had to be in the yard how it was definately nice to have someone else paying for the repair