Broadway Ave wouldn't become a freeway, my bad LOL. But I would make Broadway Ave part of the hypothetical Route 77. Technically Broadway Ave is the only Highway in Winnipeg without a Route Number. Also too, TCH 1 would continue onto the James Richardson Parkway. Broadway would stay as is, while JRP would be an arterial at-grade expressway similar to Sterling Lyon Parkway. But JRP would be a better airport connector to downtown Winnipeg than Portage and Route 90 is. Portage Ave could focus on businesses, bike lanes, and BRT (ultimately LRT), and JRP could could be focused on traffic flow with multiuse paths away from the road. Portage Ave can be the street, while JRP would be a road.
One thing I didn't mention is that possibly building these roads, some may think it could lead to urban sprawl, but I feel it could possibly help reinvent the areas. It could encourage either renovations of the older houses or building new apartments. We haven't really seen much of an Apartment Boom out there like on Pembina. No, I don't expect Winnipeg to look like Todayland (from Meet the Robinsons) or Telosa, but we need a bit more vertical living near the downtown area. Similar to connecting Hurst Way with Jubilee Ave.