I've been thinking a lot about the cabin lately, and I think that I have figured out what may have been going on and what the ash circle was for. Forgive me if this is a bit long, but I want to try and get all my thoughts down. I'll start with what we know for sure about the cabin.
MIB was definatley using it in season 4. Jacob has lived in the statue for at least 150 years so he likely never lived in the cabin, but his knife was inside and his bodyguards went there first, so he most likely has used it. There is an ash circle around it, which at an unknown point was broken.
We have seen ash circles used on 2 other occasions, with Bram and the Temple, and I belive that watching MIB's actions with those 2 can tell us how the ash works.
Starting with the Temple, the ash circle around the temple was NEVER broken. However once Dogen was no longer inside it, MIB could freely enter.
The same applies to Bram, whilst inside the circle MIB could not touch him, however when the debris caused him to fall outside it, MIB flies directly over the small circle to grab Bram and kill him.
I belive the ash circle is harmless to MIB unless someone of significance is inside it. Obviously not just anyone can use the ash, as there were still at least 10 others, Miles, Claire and Kate inside the Temple ash circle but purely because Dogen was no longer in it, MIB could cross it.
Back to the cabin, we know from Ben's dialouge with Jacob, that Richard was passing notes from Jacob to Ben during his leadership. It is worth noting that Jacob and Richard have both stated that "no one enters the statue unless Jacob invites them in". I belive the cabin was used by Jacob as a meeting place. The ash circle is to protect Richard (or whoever Jacob is meeting) during these times.
Evidence to support my theory : Richard is told you have to be invited in to the statue in 1867 and in 2007 he opens the door for Flocke and Ben yet does enter implying he has not yet been invited in. Judging from the statue question and answer I would say Ilana knows perfectly well where Jacob lives. But she was told specifcally to meet with Richardus, so she heads to Jacob's meeting place the cabin, where she finds that Jacob has not been in a long time and someone else (MIB) has been using it.
In closing, I think that judging from the Temple and Bram. The ash circle being broken is somewhat of a red herring. It doesn't matter if it's broken or not all that matters is who is inside it. If the cabin is unoccupied then MIB could easily float straight over the ash and enter the cabin, as he did to meet with Locke. I belive that MIB could hang out in the cabin all day, unless Richard or Ilana or Dogen were to show up.
The only other people we know to have entered the cabin are Ben and Claire both of whom were inside the Temple ash circle and their prescence did not keep MIB out.
I hope that you can understand where I'm going with this, sorry if it is a bit incoherent, but it seemed so much simpler in head. I think that what I have said makes sense and does not contradict anything we have seen. Let me know what you think.