In the near future I am looking to fly from Western PA to Canton Michigan. A direct route takes me into Canadian Airspace, but not landing, and saves at least 45 minutes of flying time. Researching it says that you need to have an “active flight plan”, be talking to ATC when you cross the borders, and have a discrete squawk code. When doing VFR flight following, 2 of those items will be happening, but is VFR flight following considered an “active flight plan”?
VFR flight following is not an active flight plan. FAR 91.707 requires filing a flight plan unless otherwise authorized by ATC. Since you probably won't know that until you are talking to them, you can at least meet the regulatory requirement by having filed the flight plan during pre-flight. Additionally, Canada has a flight plan requirement when operating in their airspace.
An “active flight plan”, when speaking about VFR flight plans, is a flight plan that you have filed with Flight Service and then activated or opened with them. This can be accomplished by calling FSS on the radio once you're airborne or by using their “EasyActivate” service. You can sign up for this service on their website 1800wxbrief.com . Flight Service has posted a video on their Facebook page that explains the service. And here's a screenshot of what it looks like on their website;
You can also activate a flight plan with Foreflight, FltPlan.com and probably other services.
One thing you overlooked is the need for an FCC Radio Station license and Restricted Radiotelephone Operator's license. These are required when communicating with foreign radio stations.