Bloodrose said:
You're right, it is complicated. Dual intent is an awkward process. It isn't technically a crime (nobody can prosecute you for wanting something) however when you're issued a temporary residence or work permit, the Canadian government expects assurances that you will not remain in Canada illegally afterwards. Likewise, the official stance is that you shouldn't be using international study routes to permanently immigrate (although millions of people worldwide have done this over the years through a variety of methods).
Tbh, I wouldn't overthink this if I were you. You may not even want to stay in Canada forever once you arrive and the laws on PGWP's can change abruptly and without notice, making routes from PGWP to PR pretty much impossible. Studying in Canada as a foreign student is expensive and is something that should only be done if you have a lot of surplus funds, actually are interested in that field of study and are prepared for the possibility that it might not lead to automatic PR and eventual citizenship.
I think Europeans usually have an easier time than most other nationalities at proving there is no dual intent involved however in your case that US overstay is going to be a big problem and I wouldn't recommend trying to cover it up. Part of the PR application process requires you to list all of the countries you have visited in the last decade and for how long. AFAIK an overstay in America doesn't automatically make you ineligible for permanent immigration to Canada but lying on a TWP or study permit application will.
I am really surprised by this post. So much of what you have said runs counter to what the federal government itself has said is the intent of the economic immigration programs regarding students.
The government has repeatedly said that they want to attract international talent at universities and then retain them as PRs to fill critically needed jobs in Canada. That's why they revised the CRS in November 2016 in order to give international students an edge in EE.
From the latest report:
These changes have helped to attract top talent in the world, including former international students, experienced professionals and talented workers who will strengthen Canada’s competitiveness in the global marketplace.
With these changes, more former international students are able to transition to permanent residence through Express Entry. Former international students are a key source of candidates in Express Entry because of their age, education, skills and experience. In addition to the time already spent in Canada, integrating into Canadian society permanently will be easier because they will have established social networks and they will have familiarized themselves with life in Canada.
Your notion of "dual intent" is misapplied here. If you come to Canada to study, earn a degree, then obtain a PGWP, and eventually apply for PR, then you have followed the immigration laws. If, however, you come to Canada to study, but really you were trying to get into Canada for another reason, like spousal sponsorship, be with family, circumvent a tax liability, etc, then you misrepresented your intent to study.
There can be little doubt that the intent of a PR applicant is to remain in Canada, permanently. Any previous infractions on immigration intent for temporary stays are really irrelevant, except for evaluating character. This is why I recommended the OP be honest and as detailed as possible because VO has a lot of discretionary latitude.
Given the above statements from the government, there is no reason to expect that the laws for PGWP or PR will change drastically or immediately, beyond what is already proposed in bill C-6, which actually lowers the standards for becoming a naturalized citizen.