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I am in the greater Chicago area, know Whalers fairly well, and I would not touch that boat.

First of all, a painted boat generally means it was a beater, with bad gelcoat surface, and the owner took the cheap way of fixing it up, paint. You have no idea of what repairs were made under the paint, nor of the quality of the repairs or paint job. Bottom paint means the boat was left in the water for months or years, exposed to the weather, which is why it was probably a beater in the first place, as mentioned. Also, the boat and console have been heavily altered, rails and other original parts missing, which also means a beat up boat, not well taken care of previously, re-fitted with aftermarket stuff. The transom modifications alone are a reason not to buy - real hack work. They didn't even know enough to put a proper binnacle engine control on it with separate key switch ignition harness. Note the crude cable work.

These boats have little re-sale value and generally do not hold up well.
It would be a really bad choice for a first time boater, as someone else also mentioned.. Find something in better ORIGINAL condition. Don't fall for a big, homemade fixed up boat like this, even for a cheap price.