It probably doesn't matter. I mean, the ability to convert is to ensure that you have coverage after you leave the job. Since he still has the job he still has the group coverage.
What about short-term disability and long-term disability? I don't believe that he ran for council merely in order to keep his extended health, dental, and life coverage, but given that he got sick while he was still Mayor is there a disability plan that he could have gracefully relied on once he was diagnosed with cancer without running for office again?
The answer to the disability question is somewhat complicated.
▶️You can not go on long term without first serving the short term period, which for the city is 3 months I think.
▶️You have to still be an active member to apply for, and get long term disability. There is also typically a provision of 2 years own occupation disability after which period one must be disabled from performing ANY occupation. "Any Occ" policies are very rare.
If short term disability is 3 months, that means long term disability only kicks in in early December. If he is no longer a member of council then he is not active and can't receive disability. Unless there is a specific provision for a situation like this where the plan member goes on disability during election time, he'd have to run to maintain continuity of benefits.
Alternatively, if the benefit plan may be written such that if you are already on short term, regardless of election you can apply for long term but I doubt that.
Rob is also eligible for severance of a year, during which period benefits continue, although typically disability benefits cease after the statutory notice period, which in his case would be 8 weeks.
ETA: I see the eligibility for long term is 6 months of continuous disability so if not reelected, definitely would not be an active member. It's also important to note that when one is on disability, one does not works as MINO purports to.
All this to say that there are many variables and without reading all the plans to understand what all those variables are, it would be hard to say with certainty.
Given how well thought out many rules and regs are relative to elected officials, I would not be at all surprised if an election time disability and how that's handled was not anticipated and provided for.