First off, Quebec:
This flag has a lot going for it; only two well contrasted colors, a basic design, and symbols that perfectly represent the province. The fleurs-de-lis on this flag are free from too much detail and it is difficult to see another province (or state even) laying claim to them the way Quebec can (maybe Louisiana). Plus, and this is a big one for me, Quebec's flag shares its template with the flag of Martinique, a French island in the Caribbean that uses coiled snakes instead of the fleurs-de-lis:
Too bad they aren't fully independent or they would shoot to the top of the flag rankings.
Prince Edward Island's flag is a tough nut to crack:
On the one hand, there are a number of things that can be criticized, most notably the detail given to the lion and trees. On the other hand though, I really like this flag, British lion and all. Maybe it's because it has a sense of self deprecation (We're so small, we can only fit four trees in the whole province!) or maybe it's the alternating red and white along the border. Whatever it is, my fix for this flag is a bit of a cop out:
As with others in my Canadian series, I've removed the lion. This flag is quite similar to the changes I made to New Brunswick's flag, with the notable exception of some changes to the background. The blue is meant to be the sea, nothing more, and while the trees should be simplified, the detail they provide is not wholly unwelcome (in this one instance). The three saplings contrast nicely with the mature tree bearing acorns, and whatever the symbolism, I just think it looks good. Plus the blue accentuates the border, separating it from the numerous flags which add a fringe in an attempt to class-up their flags (or whatever that's for, I don't know).
Two more provinces down, two to go.