I really like Valldore Nal's and darkraptor's ideas and perhaps they can be combined. Depending on the resources being harvested, the tool could break and the chance of harvesting a "usable" piece of the resource can decrease as the number of available resources decreases.
So if you're cutting a tree down, since it's hard material and you're using a saw to cut it, that could have a higher chance of damaging the tool when using it. Conversely, when collecting plants in a basket, that should have a smaller chance of breaking the basket as you're only really using it to put plants in it (though of course, you can always trip and fall and break it, or pierce it with a sharp root and damage it).
Further, as you pick more and more of the leaves from the basil plant, there will be less and less quality leaves available to pick from that are good for cooking, so the chance of you "spotting" another good leaf to pick should decrease. In other words, when you have just the stalk and one leaf left on that stalk, the chance that that leaf is actually a good quality leaf is small and you will likely throw it out instead of keeping it (thus failing to collect)
Another example, as you keep trimming branches on trees, there would be less "easily reachable" branches that you can get to (perhaps you need to climb the tree now, which takes more skill than just cutting the branches at the bottom).
Of course, your skill in that trade would help you mitigate these effects.