The right answer is very dependent on the condition of the boat. If the boat has decent sails, and the engine is well maintained, has decent compression and has been converted to FW cooling, then $5,000 sounds like a good price for a Wanderer which was one of the better sailing centerboard boats of this size and era.
Under no circumstances should you buy this boat without a survey. Boats of this age can easily have problems that are several times more expensive to than the boat would ever be worth.
In terms of delivering the boat, depending on where the boat is located on the south shore, I would suggest that if you are experienced sailors and you pick your weekend it should not be all that hard to sail from the south shore of Long Island to Connecticut. Growing up sailing on Long Island Sound my family generally sailed until the weekend after Thanksgiving. I would plan it this way. I would plan to sail the boat back, but budget to ship her home or hire a delivery skipper. If the weather cooperates, sail her home. If not the you are stuck paying to move her.
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Curmudgeon at Large- and rhinestone in the rough, sailing my Farr 11.6 on the Chesapeake Bay and part-time purveyor of marine supplies