I grew up on wood boats and remember that whenever we got a new boat, my dad would go through the trouble of stripping off all the old paint on the hull and superstructure by using a blow torch and paint scraper. (Environmentally , I don't know if you can get away doing that anymore.) It was a mess, but it showed him what he was working with. And as noted, wood boats, especially those that have not been in the water for a while need to swell in the sling, overnight or at least until they stop taking on water.
Good luck with the lady and remember that it's a lot of work, but it's a labor of love!
Lady C