Coming back to this wooden boat that Andrew is interested in, and is viewing this Saturday, I think, I don't discount it completely. But it needs a careful inspection first, to establish its condition.
Step 1: haul out and pressure wash inside and out, to see what the water jet dislodges.
Step 2: go all over with a probe (a thin screwdriver will do), looking for the soft spots. Many years ago, my boss asked me to go and look at a wooden boat that was at least 100 years old, that an impecunious young relative of his wanted to use as a houseboat. I went over it with a probe, and found that the outside of the hull was a bit soft but not rotten. Inside, though, I was able to plunge a 5in probe up to the hilt in the top of a frame below a hatch - fresh water had got in and rotted it. Check the build drawings and actual for hull fastening material - if bronze, OK, if steel, abort the mission.
Step 3: once that's complete, cost the structural repairs and check that they are within a reasonable and acceptable time and money budget. I'm guessing, but it looks like at least a new cabin top to build in marine ply and epoxy/glass.
Step 4: if that looks feasible, make a nominal offer of $1. Not more.
Step 5: if accepted, get a professional condition survey before handing over your dollar and completing the sale - disposal costs would be high, if it's not worth proceeding.
I wouldn't consider converting to JR, though - it would be very expensive, as a proportion of the total value of the boat, the staysail ketch rig should be manageable enough and the current sails are in good condition (though all the rigging would need replacing).