Thought about putting this in the bug forum but I guess it could also be a feature.
Whenever you get "All Thine Hard Work" you get +3 points to every item you have on you.
If you are carrying 4 Masterwork Nordic Champion Swords (you can never have too many swords!) then one "Hard Work" = +12 points to that one item.
And yes, I verified this. I had two stacks of throwing axes and got +6 to throwing axes in one message.
Argument for "It's a feature":
Whatever you want to pay the upkeep for, you can gain skill in. If that means carrying 4 swords around, so be it. Not really a big deal anyway.
Argument for "it's an oversight/bug":
It's biased in favor of weapons, especially 1 slot weapons. You can't carry 4 Huskarl shields or 4 helmets or 4 two-handers so it will be easier to get cheap one-handers than cheap two-handers. Also, do we really want to encourage people to run around with 4 swords just for this reason? How many of you are logging in right now with 4 shields because you really want to try for +12 on Elite Cavalry Shield in one sitting? Maybe you should be limited to +3 points per item per "Hard Work" regardless of how many of that item you are carrying.