As others have noted a 36 inch 2x2 is a bit heavy. I think you could easily get over the tongue weight limit of the hitch. If I had a 92 truck, I'd buy an upgraded hitch if for no other reason than to get different tiedown mounts.
But, fwiw, my 2.5 extension is less than 24 inches. My ball mount + extension could easily get close to 36 but the extension is a lot less for my 9 1/2 TC.
So I think the question is does he really need a 36 extension?
If the boat is really light, then maybe he could use two 18 inch extensions or similar. I wouldn't personally do it.
Another option is to extend the trailer tongue and let it ride under the TC bumper.
