The realistic thing is to get a relatively 'hard' budget for this new boat, then shop for that, either all at once or in parts. I know that with a new baby, boating budgets have to take second or third place, no question there! But I don't think for the price you'll ever match the combo of the boat listed above -- gaff spars and mainsail, wood hull with strakes (only 2 but hey, who's countin'?) and a functional trailer.
For a perfect Swallows & Amazons lapstrake hull in good condition on a trailer, either solid wood (rare) or ply, you'll pay at least $1500-2k at minimum. For the sailing version of same add at least another $1k. Costs to rig it yourself will be more, as gaff sails are rarely found used so you'll have to buy a new sail or kit. And the spars and hardware will be a bit more, too.
I keep an eagle's eye on Craigslist and Latitude 38 listings, and scan eBay routinely for similar boats -- and a multi-strake sail & oar boat on a trailer is rarely under $4k. The extreme deals that occasionally pop up need to be moved on in a matter of hours, not days -- that's how I got that great deal on the Cosine Wherry in San Jose. But I don't think you'll see what you seem to be looking for out here more than once a year at best -- quite rare.
In case anyone (everyone?) is confused about Kristopher's current boat, here's photos of him getting ready to literally sail circles around us at Big Lagoon '09 -
