You will need to ensure that you extend your stay as a visitor when the time comes assuming you got a default 6 months entry, so about month 5 for an application to extend. Going to the border to refresh your stay not generally a good idea as no way to predict successful reentry, but that would be a personal decision.
Having an outland application is not an issue even whilst you are in Canada in fact many people go for outland given it gives them the flexibility to be able to come and go if they need to whereas with an inland application apart from short trips it can become an issue sometimes.
You cannot apply for a work permit on an outland application and believe the only way to do that would be a new inland application which would mean starting all over again. Given many outland applications can process in 7-8 months if uncomplicated applications despite the 12 month quoted processing time seems a shame to start over.