brainstorm

Good idea on making an arterial road connecting Dugald with Logan Ave. I see how that could work: Upgrade Dugald, Dawson, and Mission St, and build a bridge connecting to Higgins Ave. I would also extend Higgins West as a full road on part of the CP Rail Yard, with it passing under the Slaw Rebchuk and Arlington Bridge. Then it would reconnect with Logan on the land of the McPhillips Athletic Grounds.
The Wilkes and Fermor Corridor could work. In your design, the idea of it cutting through the Beaumont and Okenwald neighbourhood is a bit iffy. I'd say connect Jubilee and Wilkes via Hurst Way, and upgrade Jubilee, Dunkirk, and Fermor to handle a 70km/h design speed. Jubilee may be a little hard due to residential neighbourhood disruptions and could trigger some opposition, but it could work.
And extending Waverley as a two-way arterial to Academy is a good idea. Although I envisioned making a full two-way Waverley/McPhillips connector too, I feel like just using Academy, the Maryland/ Sherbrooke, and Notre Dame could make an okay Waverley/McPhillips connector. Also, it makes sense because there's already the pair so close to it.
The St Matthews proposal seems to connect to Salter Street. Not really sure about that. It's cheaper to have St Matthews connect with Portage and a little more functional.