Opinions Please: 1940''''s Wood vs. 1960''''s Fiberglass
A lot of this answer depends on you. I have owned both wooden and fiberglass boats in my life. If you try to maintain the fiberglass boat (especially a 1960''s era boat) in the condition that you must maintain a wooden boat, it is about the same amount of work. The difference is mainly if you let something go on a fiberglass boat it can be brought back easily. On a wood boat it is harder to bring things back.
You live in an area with a comparatively short sailing season. If you are handy and enjoying messing about with boats, the winter becomes a fun time renewing finishes and making repairs. If you are not handy or don''t enjoy working on boats then the winter becomes a time of drudgery or a lot of expenses.
Boats of the 1950-1960 era (wood or glass) give up a lot to more modern designs. They are comparatively cramped and hard to sail. They are slow and wet. They don''t handle heavy weather as well as more modern designs. (I routinely sail on boats of both eras)
Launching a wooden boat in the spring is always a tricky business with the boat trying hard to sink before she swells up.
Then there is the matter of sailing in fresh water. Fresh water actually takes a harder toll on wood than salt water, but is easier on fastenings and hardware.
Wooden boats of the 1940''s and 1950''s were at an awkward time. Boat designs and constcution techniques were at a point of change from the pre-war thinking. There were some really lousey boats built in the 1950''s as designers played with their ideas of the future. This was not a time of great across the board classics. On the other hand there were some neat boats built in this era as well.
The really bad news is that boats of this era (wood or glass) are approaching the point of needing major refits (Boats that have been through total restoration are probably more than your price range.)Its not hard to visualize a boat of this era needing some combination of refastening, keel bolts, standing and running rigging, new deck hardware, new sails, new galley and electronics, and engine rebuild or replacement, new upholtery, some new planking and sistered framing, and so on. Depending on the mix this can quickly double the cost of buying either a wood or glass boat.
With both a detailed survey is critical. If you buy wood you need to have a surveyor that really knows wooden boat construction.
To me owning a wooden boat (or an early fiberglass boat for that matter) has its own aesthetic. You give up a lot but older boats give back their own kinds of rewards. If that appeals to you then by all means pursue either. Keep a reserve of a third to half of what you pay for the boat for repairs and upgrades and enjoy your piece of the past.