So are you suggesting I get a beater and the 2008? Or just get the beater because if I did that I'd just buy boat #1 most likely because all the boats I see listed around me are from the 1980's anyway. Sorry I'm a bit confused on your post please elaborate.
Yes...get both.
But get the 2008 before someone else grabs it. If I were closer it would be me. You might even be able to negotiate a better price. Try it.
Then search for a beater with a decent trailer...and a mast of course. Take what you need and sell off the rest in pieces. EBAY is your friend here.
Take what is left to the dump unless you are a hoarder.
Enjoy what seems to be essentially a new boat.