There is usually not enough water in the wood core to cause any noticeable expansion on the deck. You should use a moisture meter and a phenolic hammer but both require at least a little skill in using them properly. Both of these will be pretty useless below freezing though. You will need to wait for a stretch of warmer weather.
A '74 SJ21 should not be going for more than about $2,500 if it is in excellent condition and also includes the trailer. The biggest issue I have read about was oil canning on the hull from the trailer bunks but this would correct itself once in the water for a little bit. I personally never had this problem with mine though.
Check the centerboard to ensure it still moves in the trunk. They have been known to get wet, expand and cause some damage. Very common to have to replace the cable and
winch for the CB also.
These boats are fairly cheap to maintain. Make sure all the
rigging and sails are fairly recent. I remember replacing all the standing
rigging on mine in the early 90s for about $450.
See the following link for lots of good info. You may even find some references to the boat you are considering.
Jim Hubbard's San Juan 21 Sailing Page