33 WCF is not my favorite, but I don't have a 4-generation gun going on 5, either (at least not 5 generations in my family). If I did, .33 WCF would be my favorite
If I was that kid, I know that's the gun I would want to hunt. And I would stick my hunting license up under the buttplate afterwards too. (I know there is no hole there, but there could be).
The closest thing I have to your 86 is a 97 Winchester 12 gauge (3 generations), and it has licenses dating back to 1917.
Well post a picture of your son, the gun, the deer (if there is one), and all three!