Re: Cost to Replace Chainplates? Should I Walk Away?
If I understand correctly, all of the standing rigging of a typical sailboat can only be absolutely counted on for 10 years. After that, you are officially "on your own".
Since it sounds like you are in the market for a used boat well beyond 10 years old, and you are going to: "My intent is crossing oceans and voyaging for many years." and with your statement: "I build/repair inspect aircraft for a living.." everything there says you will be replacing the standing rig, including the chainplates.
Compared to rebuilding a plane, replacing any chainplates should be childs' play to you.
I loved your statement: "I realize I'll need to do a refit. I'm hoping not to do a massive years long refit turning into a money-suck. That would be dumb."
If you are doing a refit, it will be long and will cost a lot. Calling this reality "dumb" is "funny" at the least.... :-)
Good luck in your purchase!