Both of us are visa exempt, but would I be able to look for work, and if I was able to get an employment offer, could I then submit an Application for a Work Permit Made Outside of Canada? This would allow us to live together and still support each other financially.
If the employer gets an LMO proving that he couldn't find a Canadian or if you are the right age to apply for a working holiday visa, then you can work. Otherwise no but many other couples have faced the same problems and have lived on one income for a year in order to qualify to apply as common law. Not being able to work is apparently not considered an immigration barrier preventing you from living together.
Another question (sorry i have millions of them), do you have to be married at the time of the married class application, or can this be done during the processing period, because if this was the case, we could apply now under this class whilst start divorce proceedings.
In order to apply as married, you must be married. You can not apply and claim that you are getting married in the future. They would either just shelf your application until you do or return it to you and tell you apply again when you are married.