To keep Ma Ford's political "dynasty" going, Mikey should probably stay put as trustee. He can be media trained in use of prepared statements, staying "on message", and saying "no comment". By 2018 he'll be the incumbent, and barring any weighty scandals, he'll be set for a long time.
For the by-election, don't be too sure Doug's gonna run to the rescue. I'd watch out for one of Doug's elder daughters to run.
For one thing, she will get cut some slack because she's the next generation and is not necessarily the dick her uncle or father were at CH. So, benefit of the doubt, at least of out the blocks. For another, I can hardly wait for the Kardashian and Selfies crew: "OMG! I just had my photo taken with K-Ford!!!"