Cal 20s are good solid boats, though obviously quite small. You should watch for all the usuals, delamination, leaks, rigging conditions etc as these are all pretty old boats. For under $2K you'll get some fun sailing with these boats and there are a lot of them around if you ever want to get into some class racing. Also, with the seller being a 2 boat owner I suspect you can safely offer something less. These were the boats of choice for the old Jibset Sailing school, which had a standing offer of a prize for anyone who could actually knock them over - very stiff boats.
One thing, though, with moorage at Lynnwood... Mooring on the North Shore puts you between two bridges, each with considerable tidal currents (often flowing faster than your boat will travel) This places some restrictions on when you can leave and return to your marina, careful attention to tide and current tables is required. In your case, as sailing is limited in the Harbour itself you'll need to go through a bridge narrows either way. English Bay is the better part of an hour with neutral tide, with Indian Arm half that distance through Second Narrows.
In order to make sure you can safely transit these areas you need to be certain that the outboard engine is reliable and powerful enough to help you get through the inevitable times when you can't quite time your passage for slack.
I suspect that, if this all works out for you both, it won't be long before you're looking to move up, but this may be a good way to "test the waters" as it were. Good Luck!
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)
1984 Fast/Nicholson 345 "FastForward"
Last edited by Faster; 02-13-2009 at 09:03 PM.