Re: 2004 bayliner classic 195
Drilling holes into the transom and/or stringers is the best way, but for some reason, most sellers are too crazy about people doing that...
Instead, you can take a long screwdriver and probe into any exposed part of the transom to which you have access. Best places to check are around the keyhole (where the outdrive sticks out of the transom), around the lower section of the transom near the hull (where water would collect) and near/below any thru-hull holes like ladder bolts, etc., especially those near or below the water line.
Check stringers and bulkheads anywhere they are exposed... possibly in the engine bay or via the ski locker.
Check for ANY soft spot in the decking. If you can feel it give when you step on it, it's soft.
One thing to keep in mind: a boat stored outdoors or in an unheated space will be less likely to show soft spots, as wet, rotten wood will freeze hard. Always better to check out a boat that's been stored at above-freezing temps.
I live a little down state from you, and that boat is in the range of expected prices (maybe a bit toward the high end), esp. if it's in really, really good shape. The size of the motor would move the price down a bit, I would think. I would think you could get it for $7000 or less. If the boat's not in really good shape, though, it's really overpriced. Always hard to tell from the pictures... they always look better in pictures.