I have these for him to check out:
http://hartford.craigslist.org/boa/1643486895.html
http://longisland.craigslist.org/boa/1649178064.html
http://newyork.craigslist.org/lgi/boa/1640921738.html

Im trying to get him something that will be on the site so when he wants to move up he can come check out whats on here instead of say scream and fly that is small stuff and mostly outboard.
-Mike

This would be my pick. Donzi 18 Classics have a great ride and are beautiful boats. In my opinion, of all the other boats, this would probably be worth the most after a resto.

Coolest boat of all the suggestions too!

Mike a year and a half ago I bought a 1991 Donzi sweet 16 in mint condition for $ 6,000 , it runs 45 mph and handles 2 footers like a 20 foot boat . Best deal on a boat I ever made . Great for skiing the kids ,tubing and just going for a blast and it looks cool, a 16 foot veresion of an offshore boat.

Rick G.

I have an 87 Checkmate with 210hp 4.3 with alpha,runs 55 all day long on gps and is a blast to drive.I believe its 17.5' in awesome shape.It could be had for 3500.00

A 18 foot Powerplay/Powerquest is a big little boat that can handle some rough stuff. They mostly came with 260s and will run 60 with it. Well built and Michigan has a ton of them that i am sure you could pick one up in decent condition for that price.

i sold a baja 196sport last summer for $4800, it had a 454 alpha setup and would run 67gps on a good day. not to many around but it was a good boat to me.