I think the problem most "visionary" candidates are going to experience if elected is money. The City simply does not have the current revenue needed to drive transformational change. It doesn't matter if your vision is enhancing transportation (free-flowing ring road, full BRT system, LRT, or metro), helping vulnerable communities and homelessness, building community centres and parks, or building a vibrant downtown. To make true progress on any of these initiatives in a 4 or 8 year timeframe would require tens of millions of dollars. Most City departments are on a shoe-string budgets and there is very little money to be re-allocated from existing operations to fund new problem-solving ideas.
Look at this image below (taken from city budget documents) that show how each department's budget has changed over time. It's quite clear to me that besides police, fire, and road repair, everything else has remained more-or-less stagnant since about 2010.
And if someone wants to make serious change without levying additional taxes by taking funding away from Police and/or Fire, while there may be some merit to the conversation, an intelligent mayoral candidate would need to acknowledge that a trade off will exist. Yes, Police and Fire employees are paid very well, but these salaries are somewhat in line with other Canadian cities with similar cost of living. So how do you reduce their salaries without retention problems or union interference? We all know police and fire unions are some of the most powerful in this province. And if you reduce staffing in these departments, they still have essential roles to fill which means more overtime on existing staff which will end up being even more expensive. Police are very busy as-is, and aren't sitting around browsing the internet all day. You can't remove some of them without impacting safety and levels of service.
Whether blue-collar fiscal conservative boomers like it or not, the fact of the matter is that Winnipeggers are under-taxed at a municipal level (low property taxes, no development charges) and over-taxed at a provincial level (high income tax, high payroll taxes, and high education property tax though this is changing but at what cost). And without a "Winnipeg-friendly" provincial government, there will be a strong fiscal imbalance between what the city can do and what the province can help out with, but refuses to do so.
Compared to every other major city in Canada, Winnipeg has the lowest municipal property taxes for average homeowners, the lowest revenue per-capita, the lowest expenditure per-capita, and property taxes as a share of homeowner income are also the lowest. I find the below comparison quite telling in explaining why, at a municipal service and infrastructure level, Winnipeg has fallen so far behind other Canadian cities.
This is a fundamental issue in municipal governance that no one ever seems to address. We just seem to elect populists who promise endless "efficiencies" to stave off much-needed municipal revenue growth as we fall further and further behind our peers, but you can only squeeze departments so much. We are at the point where actual "efficiencies" for the public service like software and hardware upgrades - things that would enable departments to do their jobs better and faster - are not approved because there is no budget. So you save money in the short term but build a less efficient and less competitive working environment over the long run.
My point is that it doesn't matter what your vision is, unless your vision is status quo and keeping taxes low, you will enter the mayor's seat and you will quickly find no money to accomplish your vision. And because we've kept taxes low for so long, there is very little room to maneuver and re-allocate without significantly disturbing existing service levels for roads, police, fire, parks, etc.
Significant change would have to be funded through a large policy shift most Winnipeggers wouldn't be used to or support: property tax increases in excess of 4% for several years, significant borrowing of debt to fund more capital, and the exploration of additional revenue sources like a properly-implemented development fee to offset servicing costs. We've hamstrung ourselves over the last 2 decades by keeping municipal revenue low to the point where meaningful change will be very costly both financially and politicly. And one-off stories in the media such as the building inspectors taking extended lunches or the traffic signal debacle - while valid and should drive organizational change - only cement the idea that the public service is lazy and incompetent, only there to burn your tax dollars, so naturally people are very wary of lending the city more money if they believe it will only be wasted even though these stories are far and few in between.