There is no problem overlapping work history, or work and school history. Each entry stands on its own. Main thing is to avoid gaps; that is do not leave any months with no reported activity for the month. It is very common for people to have overlapping jobs or overlapping school and work.
Overlapping address history is more tricky. Generally people are thought, considered, to have only one residence address at a time. For those who have maintained a stable household for most of the time, and that is the physical location where they stayed almost all the time, address history is simple. Beyond that, however, the variations are so many it is impossible to describe a single approach which will cover even a large percentage of other possible situations, let alone most, let alone all. The details can matter, and the details are specific to each individual.
Which leads to more general principles or guidelines when completing forms like this: giving the best honest answer you can, based on your careful understanding of what is asked and how to truthfully, accurately respond based on your particular facts. Many times there is no one right or wrong way to do this. You give your best answer.
You have identified the secondary concern, that is the risk that listing an address in one location which is not consistent with the work history history for that period of time will raise questions. The primary concern, of course, is to give an honest, accurate answer.
My sense is that there should be no problem with overlapping address history, particularly if a separate page is included explaining why. Be very brief. "Listed overlapping addresses because I worked away from home."
Another approach is to list primary residential address (some think of this as their legal address) in the address history and include a separate page listing secondary addresses with dates those address were used, either as to specific date ranges for continuous stays of a month or longer, or longer ranges with description of when that was where you were staying.
For example, on separate page: list XYZ address January 2014 to April 2016, boarded (stayed) here xx nights per week (or month) while in ABC city for work (school or whatever).
BE VERY BRIEF. Stick to essential facts.
Nothing to fret about. Nothing to worry about. What is far, far more important for a PR card application is an overall history which indicates the individual has settled permanently in Canada.
