I have owned and maintained several wooden boats in my life time. I found that wooden boats that are in great shape are no harder to maintain than a similar size glass boat kept in the same condition and there''s the rub. Few fiberglass boats are maintained in the condition that wood boats require if they are to survive. With wood maintenance must happen when the boat needs it and not when it is convenient to you. Fall behind and it is a foot race to catch up and often a loosing race as one part after another fails as you race to replace the previous part that needed help.
At the core of your question is the issue of the specific boat in question.
Who designed her and who built her will shape the engineering of the original boat and the quality of the original workmanship.
What she was constructed of will shape the inherent durability of the boat. Teak over oak with copper rivet construction or cold molded cedar are nearly permanent construction techniques. Mahagany over oak with galvanized fastenings is a dead boat waiting to be landfill.
Her original purpose also has bearing. A light weight race boat out of the Herreshoff yard was a beautiful piece of engineering never intended to still be here a 80 plus years later. A heavy weight workboat type hull also was never intended to be here either as the heavy timbers are harder to keep dry and prevent from rotting. Durability lies somewhere in between.
Then there is age. A well built wooden boat can and will last longer than any fiberglass boat that I know of- sort of. A properly built wooden boat can be maintained almost forever but it''s a bit like George Washington''s Axe- a few new handles and a few new heads but it''s still George Washington''s Axe. If you see what I mean. When I was growing up, it was not that unusual to hear of boats being refastened. Then replanked, then reframed. They might get new keel bolts, deadwod, floor timbers (as I had to do on my Folkboat). They might need new rigs, and rudders- a new interior and cockpit also as I did on my Folkboat) Over time someone either does the long term stuff of the boat ceases to be a boat. As the yard manager told my dad when I hauled my Folkboat out of the water to do the restoration,"It may look like a boat but that is not really a boat".
Of course past maintenance is the most important factor. A wooden boat that has poor maintenance thoughout its life is next to imposible to keep alive. A wooden boat that had great maintenance is more likely to be maintainable.
In your situation, if you really want a wooden boat, start with a small one (under 20 feet)so you can learn the necessary skills to own and maintain a wooden boat. Try to buy a boat building book written during the period that your boat was built. Chappelle''s Boat Building and Bud MacIntosh''s books are very good. If you are buying a cold molded boat then WEST System''s Book is handy. I would also subscribe to WoodenBoat Magazine.
In the end, I still like wooden boats. In my current life, running my own architectural firm, I do not have the time to maintain one. It might be helpful to someone replying to your question if you gave a more detailed description of the boat in question. (Designer, yard built, year built, size and design name)