I try to do one major project per year that costs between $5-10K. Minor maintenance issues usually add up to an additional $1K per year.

Last year I had my engine transmission rebuilt which cost $6K.

The previous year, I ground out and patched hundreds of hull gelcoat blisters and epoxy barrier coated. I took time off work to do the job myself, so technically it cost me lost wages, but around $3K in supplies. It would have probably cost well over $10K to have a yard do a half-ass job.

This year, I'm planning on replacing the rig with $10K budgeted.

I'm aiming to drift more toward $5K per year once the vessel is shipshape.

(Also, $6K or so on marina fees.)

Two years ago I replaced everything from the engin bulkhead aft, tanks, fuel transfer/polisher, engin, shaft, prop, water filter etc, etc for $15,005.00..........I can't remember if that included bottom paint or not.  I just got Tamzin out of the yard about two weeks ago for a bottom job, new zincs and a few grinds and patches for $995.00 (doing the work myself)

It's best to look at cost in at least two categories. The first would be your monthly costs such as berth fees, taxes, insurance and maintenance. Ours ran from around 6k to 8k per year depending on where she was berthed. The lowest was $230 at the Stockton Sailing Club to @$600.00 in La Cruz Mexico.  We're currently paying $360/month in Ensenada Mexico.

The second would be outfitting for cruising.  While there are a lot of variables the consensus is the average cost to outfit an older boat is @ $100,000.00.  We far exceeded this.  Over the last twenty years we've kept meticulous records on Quicken knowing where every cent went.  Something most new Westsailors don't really understand is buying a top dollar Westsail for $65-75K is the cheapest way.  You can get a turn key boat for 40 cents on the dollar. 

Jim