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So imagine the scenario...your guild have found a bugbear village, and have built a defensive parimeter all around it to stop anyone getting in or out. When the bugbears try to get out, they are killed and skinned, and their hides turned into guild armour. Any players trying to tresspass in are warned off or killed outright. This alone would take a huge amount of manpower.
Several game weeks pass, and the number of bugbears coming out are getting fewer and fewer, until eventually no more come out. A scout is sent inside, where he discovers that the creatures have starved to death - they weren't able to get any food, so the whole settlement died.
Of course depending on the race, they might turn on each other, or rally for a final attack (ie every last living member of the settlement charges the weakest point of the defensive parimeter).
I suppose the guild could get around that as well, by dropping off food, although depending on the requirements of the race (eg needing human flesh) that might not be feasible. Just as the settlement would need to collect wood or stone for new buildings and metal for new weapons, so it would need food for more members (as well as maintaining the existing ones).
You could also have a natural migration of settlements - some races are particularly well known for not staying in the same location for long. You could "guard" the settlement with your guild, but what happens when they pack up and move on? You'd have to fight every last one of them, and you'd no longer get the exp for destroying the village. Other settlements might eventually just "die out" or from age or disease, or be force out by bad weather conditions.
Besides which, there would be a fair number of settlements/generators, so even if a few were guarded, it shouldn't prove too much of a problem.
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