Our boat will be 33 years old in February; we bought her 12 years ago. Pretty much, we bought a sturdy hull with a layout we liked, and planned to replace "everything." Because of the boat's age, her low selling price plus trucking to our then-home port, meant we could afford to do all that. It seemed our boat was built at a sweet spot of age: they knew how to work fiberglass but weren't totally convinced of its strength, so we're considerably overbuilt (1-inch-thick hull!). Heavy and slow but oh so comfy. Especially with your skills, you could do this too, and get the additional advantages of (1) being able to install *exactly* the systems you want; and (2) knowing how everything is put together, you can fix it yourself if you're out in the boonies somewhere when things go bad.
Downsides: (1) In an older boat, you won't have a hull/keel design that incorporates any advances in marine architecture over the last 30 years - maybe someone with more expertise than me can weigh in on this. Older boats tend to have full keels or modified full; how much difference in sailing characteristics will be gained by swing, bulb, or other new-shaped keels? (2) Unlike a new boat, whose value is pretty straightforward, You will *not* be able to insure an older, refurbished boat for what you have invested in it.
FWIW, there's an old Sailnet thread that touches on this topic: https://www.sailnet.com/forums/cruisi...300-000-a.html
In it, we posted the cost of our retrofits, copied and pasted below:
We replaced "everything." Everything we put in was new, mostly purchased at Annapolis Boat Show sale prices. The refit took about 2 years and we - mostly Dan - did everything ourselves except the engine, heater, and rerigging installations (for insurance/warranty reasons). The first priority was things that make the boat safer or sail faster, then, everything else (all prices in boat bucks, a.k.a, thousands of dollars)
Yanmar engine 20
Frigoboat keel cooled refrig/freezer 2
Lofrans windlass & remote switch 3
Autohelm under deck mount autopilot 5
Webasto diesel heater 2.5
replace all standing rigging 5
arch for solar panels with integral cockpit rail 5
Brig 10' inflatable dinghy with 9.8 hp outboard 5
Cruisair reverse cycle air conditioner/heater 2.5
North Sails new mainsail & genoa 5
Force 10 stove/ oven 1.5
replace fuel tanks 2
100' chain, 200' rope and Rocna 44 anchor 1.5
Those bigger ticket items account for $60K of our refit budget. The rest of it (each item $1000 or less) went for: solar panels, bilge pump & 4000 gph "Hail Mary" pump, upholstery/paint/varnish/formica, marine-grade wire, LED lighting, cockpit cushions, trifold swim ladder, bimini, stereo, sinks and faucets, Seagull water filter, 4 AGM batteries, Xantrex Link 20, 2 Garhaur 6-part purchases for dinghy lift, handheld Garmin chartplotter, and (*winks at CruisingDad*) a BBQ.
4 months into our cruise, there is not one single thing I'd change! The solar panels make all of our power needs on sunny days; we generally run the engine about 45 minutes every 4 days to make up the difference due to occaisional cloudiness. We chose not to use a generator (too noisy) and instead use extremely energy-efficient systems, like LED lights and the keel-cooled fridge/freezer, so that we could maintain ourselves with solar. We have no watermaker, but with a 100-gal water tank for 2 people, we can go 3-4 weeks before refilling. We also chose not to install radar because our chosen cruising grounds, US southeast & Bahamas, rarely have fog and we rarely run at night, therefore less need. Disclaimer: these are our solutions, for the way we like to live, I'm not assuming they'd be right for everyone.
We strolled the boat show last weekend and nothing new and shiny engendered any boat lust at all, except the Gozzard that cost literally TEN TIMES the current appraised value of our boat. I guess we did okay.