These Santanas are good entry level boats, used Santanas are readily available in good condition in the Portland area with excellent local fleet support, plus he'll be able to sell the boat again for what he paid for it.
He could pick up any of the boats I mentioned for much less than $5k, use to learn a lot
How about trying this: "Santana 20 or Cal 20. He could pick up either of these boats for much less than $5k and learn a lot. They might even think about a Thistle and maybe learn even more. Of the three mentioned, yes, I'm partial to the S-20. We build them and they have an active local fleet.