Owning a boat is like a leaky bucket?

cheer up mate sounds like you have already done the big ticket items

Don't worry you will forget all the pain after a few days of sailing. Besides, what else would you be doing with your time and money?

I feel your pain, NSW. Actually, I feel mine but it's similar to yours. I'm 3 years in also and have done more than is one your list and spent far too much. Far too much from what I envisaged and far too much to sell because I'll never get the money back. So that means... I'm committed to keeping her for the long term, maintaining and upgrading as I go, and enjoying as much as possible.

Yes, I'm afraid of the future expenses but I have almost all the big items (all except re-painting the hull). I've considered cutting my losses but then I look within and ask myself that question and the plain truth is that I just can't go back. If I sold her I'd... Well, I could I suppose. I could even be happy. But something would be missing. I have too many more miles to sail, skills to learn, whales to see, fish to eat, beaches to swim, weather to handle, places to discover, sunsets and rises, moonlit sails.... ah, the dreams, the dreams.

How long since you've had a good sail? We've had a crap autumn and winter until recently so I suspect you've not been out much. Plenty of whales around at the moment - there's even one in Middle Harbour!

And in 4 months it'll be December!

Yep, they are expensive toys. For most of us they are also old. What else that is mechanical / electrical do you own that was new in 1984 and still works?

Kmowing we are not alone helps, my list of new gear over the last five years

Anchor winch
anchor chain
standing rigging
service and paint mast
new main
new jib
fuel tank out of the boat, steam clean, reparir leaks
new prop
Wind, log, depth instruments
new back stay tensioner
new cabin side windows
steering pedestal
electric toilet
holding tank
bathroom taps / shower
shower sump pump
gas oven
hot water heater
refridgeration unit
stereo
VHF radio
battery charger and shore power set up
solar panels and regulator (two regulators, the first failed just out of warranty)
switch pannels
auto pilot
chart plotter
and finally, significant osmosis repair, out of the water for three months, peel and reglass with epoxy.

However, I started this work with a fair understanding of what was required and I now think of my 1989 boat as pretty much new, except for the hull and engine. I am putting aside $ to replace the engine, when required.

That's a good one, Cisco. 31 years, just the way he likes it. Blimey.

Owning a boat to me is transforming a machine to be an physical extension of yourself and your purpose and goals
Be it comforts , Safety and its sailing ability. and more. This also means for what purpose your crafting your vessel for , racing , cruising or a weekenda

Are we helping or making it worse, Keen?

Check this out cisco,1976 model just ticked over 300,000 three weeks ago.Ive owned it since new.

Keen, I know how you feel.
I have a 1982 Top Hat, that I vowed to never let get into a worse condition than it was when we bought it. So far we've succeeded and she's actually functionally better, but not so cosmetically, she's pretty much the same.
On the weekend, I realised the only maintenance I've done in over a year is the slip/antifoul. She currently needs the following.
Full paint job - but I don't really think that will happen any time soon.
Complete interior re-fit - to make it more aesthetically pleasing, but everything works as intended - see above
New sails, but the ones I have work well enough for our needs.
Repair to the boom bag, as the zipper stitching is failing
Varnish the toe rails
Varnish the companionway
Varnish the coach roof grab rails
Rust proof the "harbour bridge" mast step.

I also have a 1982 Harley Sturgis model. Over the last three years I've completely rebuilt the engine, gearbox and had the tin work re-painted. I still need to do the wheels, handlebars and various other smaller items that are showing their age.

Then there is the 1989 VW Caravelle (Kombi to the un-initiated) It's got 401,000 km on the clock. Since I bought it two years ago, I've replaced the starter, a muffler, fuel pump, front brake rotors and wheel bearings, tie rods, rear main seal, two oil pressure switches, throttle body, alternator, and re-built the CV axle joints. Not to mention the on-going rust patching, until I get enough time to paint her properly.

Finally, the lady wife and I are extending the house. As an owner builder. This should take about three months, but I'd lay odds on it taking at least double that by the time we actually get it finished.

Bought this Fiat 850 coupe new in 1970, only new car I have ever bought. Panels in the fore ground are epoxy/'glass.
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So thought i would add my 10 cents worth, 72 mustang 3 year build, and going very strong, sold my last mustang and bought my boat. so all good,
That is one very tidy Capri Crustysailor

what a nice collection of bikes and cars, I'd be happy with a Mustang, Fiat 850 or TR.

I won't feel guilty now not posting anything on the 'what did you do on you boat today' when I've been out in the shed because its too cold down on the boat.
HG I don't know how you do it during winter.

Maybe we sneak a garage update shot in the boat thread once in a while.