WTB: 209 Fisherman (2011-2017)

Regarding that one, there are several things that don't work for me personally including most of what you mentioned. 700 hours would certainly not concern me at all for 17+ year old boat. I am targeting a F200 inline 4 due to the weight / performance for that hull. I sea trialed a 2009 208 with a 250 and while it is a different boat (and a little heavier), the hull is the same. With just me and my 100 lb wife standing in the back, water was coming in through the scuppers. I'm about 185 (..sucks in beer gut...). That boat may have had other issues going on (including a wet transom?) but later was told by a dealer that the bigger outboards may push the weight just over the limit potentially bringing water in when standing back there. Moving the batteries into the console could help though or just wear a pair of xtratuffs?

However, that 2008 appears to very nice (possibly very well taken cared of) and I'm sure worth it to the right person, but not for me.

There was a boat up here 3 weeks ago that I missed out on. A 2017 209 with an F200 with 42 hours. It had bottom paint and the price was higher than I would have wanted to pay. However, it did not last long and was under contract before I could get to see it.
Water coming in the boat through the scuppers is most likely an indicator that the rubber scupper flappers are brittle, they aren’t sealing correctly, are warped and/or simply just need to be replaced. My boat was like that when I first bought it and I’d stand in the back of it, you’d have water starting to pool in at puddle up at your feet. Replacing the rubber scupper flappers at less than $20 total resolved that issue, though.
 
I listed my 209 here a few months ago. Do a search for "Threeputt" and you'll find it.
Its older but its a great Grady.