I just heard about this agenda item that went thru the exec: http://app.toronto.ca/tmmis/viewAgendaItemHistory.do?item=2020.EX15.5
Professionally, I'm a software engineer and entrepreneur. I don't have the time to evaluate this deal in detail but this has a weird smell to it. Questions that come to mind:
Why single sourced? What's the rush? This doesn't have a COVID timeline.
Contra staff, the city actually does hold a lot of risk. The contract may expire in three years, but replacing an integration that replaced 22 existing payment processes will be a significant, many-months-long project that can easily cost (a few) millions of dollars. Once we're in, it will be a lot harder to leave!