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I don't know such tool besides webmaster toold that represents rises and falls in rankings, but maybe you can get some use of this one: http://www.archive.org/web/web.php It is actually a web page archive so you can get a view on a former look and content of the webpage. Maybe this can give you some clues about the rankings.

It's probably set in GWMT to the default geo targeting in USA. FYI - I have have excellent success with .ca sites ranking in Canada. The competition is SO much less than in the USA. It takes very little work to get a .ca domain ranked in google.ca, but then again the traffic is just not there. You say it is a Canadian company, but is it a local type business or is is global, do you ship to the US? If you ship to the US you will find a lot more business there and ranking in Google.com in the US is much more beneficial. If you do ship to the US, then I would suggest not being obvious about the fact that you are a Canadian company or people will be more hesitant to purchase from you.  But in reality a Canadian company can easily ship to the US unlike some further countries where shipping cost is much higher and time takes much longer. It all depends on your type of business.

Not entirely sure how this system works, but i would think that if the express-lane content had search/content benefits then adding it as a folder would be a better option. As subdomains are treated as seperate websites, if the content can benefit your root/main domain, better off giving to kudos to that rather than to a standalone subdomain site.