So, to the original poster, nobody here has professed previous ownership of either a 36- or 42-foot wooden Grand Banks, the specific boats you are considering. I do.
I bought wood because as a serving US Navy officer at the time, I could not afford more.
Everybody so far has pounded away at the excessive maintenance issues of a wooden hull, but aside from the preventive measures I took, things like spraying borate solutions intended for log cabins inside the hull and the every 18 months haul for bottom repainting (removal of all old paint about once every 12-15 years), I never found my hull maintenance any more difficult than a fiberglass boat because wooden Grand Banks were well built with 1.25 inch thick mahogany strakes and yacal framing. I pulled sample bronze fasteners over the years and never found significant thinning; so the 1972 boat I owned from 1986 to 2015 was not refastened and continues to give its new owner good service.
Now the wooden (plywood) topsides and teak deck were a different animal. I did a bit of rot removal on the cabin in the early years, but it was sound as can be thereafter. The new owner did not want to deal with the decks and so has covered them over.
I find your comment that you are considering the boats for liveaboard purposes interesting. Does this mean you d not intend to run the boat, either "cruising" or just local area use? How many would live aboard? I found the 36 too small and my 42 to be about right for one or two - I did it both ways.
You may well find difficulty in locating a place to moor a liveaboard vessel, and if your insurance company becomes aware of your status, there could be adverse impact on your premiums.
So now that I own a faster, smaller, lift-kept, fiberglass boat, you could ask why I sold the woodie. The perceived advantages of faster, smaller, lift-kept, and fiberglass are your answers.
