Coming back to the original subject, we had a discussion about this at MR, because we too have one place where you get equipment dependent on your tagged skills.
The difference is that the script chooses randomly between your tagged skills and gives you items based on one skill only. Some skills don't get anything (Sneak, Steal, Energy Weapons, Big Guns), so they are of course ignored. If all your tagged skills don't get any items, you just get some extra healing powders.
We gave Gambling a pair of dice and a deck of cards. If you want to give players cash, but don't give them caps, give them the zippo lighter instead - it's worth a hundred bucks and it could belong to one of the original dwellers, and somebody chipped it in, so you can barter it for something else. Or maybe you won the lighter in a card game in the Vault?
I also like the idea that you get a rope when you have Outdoorsman tagged. As for melee, you should give a next-tier weapon - like somebody pointed out, the club deals the same damage as the knife, so maybe give a crowbar instead.