This looks like it has some serious potential. Let me mount an offensive I haven't for several months.
Gameplay- The bonus regions feel a little bit inflated. Granted the Golden Horseshoe has a lot of connections, but 8 territories for a +7 bonus? Most of the others are similarly excessive. I would say bias toward low-bonus for the entire map and introduce a few other ways to gain bonuses (like auto-deploy territories, or "Main Hub" bonuses scattered about the map, you appear to have territories of this variety already around, add a bonus).
- The present font is actually readable on account of being sans-serif, but it's a little small. I've seen your ideas to add breakout boxes for the more congested areas, so that should help with both the font and your other issues.
- The bonus colors are different enough to be differentiated...assuming you're not colorblind in some way. Perhaps add a minimap or some other cue for what area is where (like text on the map as a region name).
- Having a negative bonus for anywhere (Bancroft in this case) is a major non-incentive to ever hold it, and could even put someone to drop it at a permanent disadvantage. Instead, have it start as a neutral of 3 or so. That'll lower incentive to hit it early on, but not keep it practically ignored by anyone struggling for a bonus.
Graphics- I like the diamonds. Seriously. They're poignant and non-distracting, and they're different from the umpteen-zillion maps on CC that have army-circled subway lines or something similar. Just figure out how to space them well enough to have sufficiently-large army circles.
- The entire map is clean, which is a major plus for a map this early on. I like the good design flow, and while it may be a little bit blank at points, you certainly can improve that in time instead of having to figure out what to take out where. Keep with the simple colors and themes, and rely on that for the map's beauty.
- A title is required. Your original draft had one, but I think you can one-up that with some subway-related imagery or perhaps some symbolism of Quebec. Be creative with your title, I've always used the title as an inspiration for the rest of the map's appearance.
I believe that is sufficient to keep you busy. Behold, even the most dormant army can sometimes mobilize and get you

.