Forget Maxum and forget wake boats of any flavor.
That Chapparal, OTOH is to die for. If I were in the market for a bow rider, I'd be all over that one! I'd try to get them to knock it down a couple thousand though, I'm sure they've padded the price by 2K for that very reason.
Other than inspecting the engine, I'll tell you what to check. Get down on the ground under the outdrive and remove the drain plug (if it isn't already) and shine a light into the hole. Is it bare wood inside there or is it sealed? If it's bare wood, then move on, that boat'll likely need a new transom in another five years or so. If it's sealed, then check the skeg. Has it been dragged on anything hard enough to remove metal? If so, then let some oil out to check for water. In fact, it wouldn't hurt to check the lower unit for water intrusion any way. How clean is the engine compartment? Is the fiberglass stained? Is there mildew growing on the vent hoses? If the rest of the boat is any indication, I'll bet the engine bay sparkles too. Look at the bolts and lugs, like on the starter motor. If there's rust, then there's been water in the bilge - which isn't the end of the world, but you need to figure out how much and for how long. If there's staining only at the lowest point below the motor, then I'd call that boat a very good candidate.
I would, however, get rid of that whale tail and install proper tabs right away!
