Membership status rules query
Sorry I thought I'd answered previously but I'm 99% this is down to the fact that once a membership status becomes ended the automated rules then wont touch it. So the first status of type ended in theory would be the one that gets applied and any subsequent ones wouldn't be something that automatically gets moved on. I'm 99% thats the issue your facing, a previous question asked if CiviRules could be used to change membership statuses (which it cant yet), your case is probably one that fits a CiviRules status change I think. Let me know if you prove the theory!