Divide the selling price by 5. How much is each year of cruising & adventure worth to you. If your only going to own it for 4 or 5 years, buy it, cruise it, enjoy it, keep it looking nice but don't be a slave to it and don't put a cent into it that you absolutely don't have to. After your 5 year timeline is up, if there is anything left of it, sell it for anything you can get. If by then it's a floating wreck, which is highly likely, take it out and sink it.
My last wood boat in the mid 1970's, a 36 Owens woody took me to the verge of bankruptcy and divorce. All my time was spent working on it and I was spending tons of money I couldn't afford. Had I just used and enjoyed it rather than trying to preserve my investment/capital cost, it would have been a positive memory for my family, not a negative one.
If you can go into it with the mindset it will be worthless in 5 years, go for it but don't be a slave to it. Use It & have fun!
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