Thanks Jeff! That's a lot of great information. At this point, I'm debating between jumping into a boat in the $2-3k price range, or saving up more money (perhaps $5-10K) for something a bit newer/bigger/better conditioned.
However, out of all the boats under $3k I've seen in my location, the Coronado 25 appears to be the best. Granted, I don't know sailboat brands (stigmas, reputations, etc.) like I do with powerboats, but it certainly shows well. I've also looked at a similarly priced Grampian 26, but it is in much rougher shape.
I'm really just looking for a starter boat that will get my family and I out learniing to sail and cruising a bit on the weekends while we dream about more southerly cruise plans for the future.