I have to side with Fender on this in some ways. I know some time was spent on this project but I don't see it feasible or necessary in any way. I've never found driving downtown from the expressway via Dougall to Ouellette a major problem. According to Google maps from Dougall & West Grand (as close to the expressway offramp as I could get) to the Chrysler building at the foot of Ouellette and Riverside is only 5.6km. So it's not really that far of a trek before you are as far downtown as you can go.
I will agree that the fact that the train lines are there do serve to sort of sever the west side of the city from the central and eastern part of the city but that doesnt' mean they don't still serve an important purpose being there.
The biggest transportation issues in Windsor have usually been moving from East-to-West and vice versa, hence the expressway. Wyandotte is a big commuter road (which by the way needs road work, looking at you Mr. Mayor). Riverside is always jammed with cars at commuter hours as well. Tecumseh is Tecumseh, a major east-west arterial with a bulk of our commercial businesses on it. Cabana I would say needs to be widened it's entire length (go take a drive around St. Clair College during school especially in the morning, or check out the eastern end at Lauzon during rush hour).
As for north-south in this city, well, they are widening Walker from the expressway to Cabana which is a good thing. As it stands right now there are no turning lanes for Walker in that stretch and there are a lot of commercial businesses there so that will bring relief.
Huron Church will eventually have less trucks (or no trucks) on it when the new bridge is built (if). Lauzon-Lauzon Parkway now moves people very efficiently north-south through the eastern edge of the city.
Lauzon Parkway does need to be extended and connect to the 401 which is the intention as the city has already done studies on this potential project.
Jefferson & Pillette are both busy roads and still move people pretty well but suffer from awkward grading at the rail tracks at both ends of South National.
Coinciding with your ideas I think that maybe both Howard and Dominion/Campbell could be bulked up to move traffic north-south in the central part of the city as both roads narrow as they approach the downtown.
When it comes to roads honestly right now I'm more concerned with the core of the city and how the Aquatic Centre now cuts off both Pitt & Chatham streets downtown and yet the western portions of those streets will still be one ways which I think is no longer needed since they are now severed from the core and that stretch of those streets is only 2 blocks long.
I'm also concerned with the cutting off of Goyeau downtown for the tunnel. I think getting around downtown is going to be a bit of a pain in the ass after these 2 projects are done and I have my concerns for those blocks west of the Aquatic Centre once they're cut off.