One that bothers me is how the war spreads to North America in the first place.
So Germany invades France and Britain jumps on Germany. Fine. Why does the CSA care? And what would it be able to do anyway?
Ship food, credit and guns to the Entente, send volunteers, be an asshole to CPs diplomacy and an Entente member in all but name but still neutral (this is Wilson after all)... still don't need declare war on Germany and Austria-Hungary for that.
So they had an alliance. Big deal. Italy had one as well and didn't jump in a war it wasn't sure its benefits outweighted the costs.
It'd make more sense if the US, sensing that it was its opportunity to settle scores now that Britain and France are distracted, went to war with the CSA again - and only the CSA.
Or if the USA decided to jump on Britain in vengeance for the 2MW, and the British (then) appealed to the Confeds and these realized that if Canada fell they would be next, and complied.
Or the USA decided it was time to jump on Britain but its war plans dictated a pre-emptive invasion of the CSA, predicting that it would invade them in response to going to war with Canada anyway, and the paralel with Europe's war would be even closer to boot!
But what do we have? The CSA goes to war with Germany for nothing. In response, the USA goes to war with Canada and the CSA. Wilson predicted that, but did it anyway.
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For the war proper, I agree that the USA should have cut Canada in two fairly early, then we could bring all kind of excuses to justify why Canada doesn't break - the USA gets bogged down in mountains/rivers/lakes/taiga forests, commits more forces to the southern front, Canadians have greater fighting spirit, American generals screw it up, Japanese and Russians send enough reinforcements to hold BC's defenses, whatever. But going by geography alone, the Americans would be in Edmonton before Ottawa knew it. Maybe Roosevelt preferred to invest all the money in other objectives and there were only small underequiped armies in the long border told to defend their border forts only, I don't know.