I would say absolutely 100% apply for the bridging work permit if you have no other option available to you. Here's what will happen: you will apply for the bridging work permit with the first AOR you received, just a few days before your 15 December deadline. That will put you on implied status with the conditions of your current work permit applying until you get either a rejection or acceptance on the bridging work permit application. In the best case scenario, in about 3 months after applying, when they start processing your work permit, you will either already have become a PR or you will have received your second AOR and they will approve it. I've heard that 8 weeks after the first AOR we can request the second AOR. YOU MUST APPLY FOR THE WORK PERMIT BEFORE THE FIRST ONE EXPIRES, TO BE ON IMPLIED STATUS. This is the most important thing.
In the worst case scenario, in three months when they open your application to process it, they will see you only sent the first AOR and you don't have the second AOR. If they want they can still approve it, but if they don't, they will send you a rejection letter and tell you that you should stop working and apply for a restoration of status. You will absolutely not be penalized for working uptill then, even if your application is later rejected for being incomplete, because as far as they are concerned, you still sent an application for a work permit before your first work permit expired. I have verified this with the call centre agent and my lawyer on several occasions. I myself am on implied status right now and have a bunch of things under processing with CIC and they have not told me to stop working.
