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Even before the ballots had been cast in Monday's municipal election, there were already rumblings among Ontario Progressive Conservatives that if Doug Ford didn't win Toronto's mayoralty, he might consider a bid for their leadership.

In the days since he lost to John Tory, Mr. Ford has made clear that his past interest in the provincial Tories' top job – expressed while Tim Hudak still held it – has indeed been rekindled by his experience on the hustings.

Before Mr. Ford launches another campaign so soon after the last one, though, there are still some big questions for him to consider – ones that help explain why most party insiders put the odds of him taking the plunge at no higher than 50/50.

Does he really want the job?

Until September, when he stepped into the mayoral campaign in place of his ailing brother, Mr. Ford was openly looking forward to leaving city council after a single term, and returning to running his family's decal business. And for someone with limited appetite for day-to-day life in public office, there might be very little enjoyment in leading a provincial opposition party.

If he won the leadership vote next May, Mr. Ford's prize would be three years of travelling Ontario, speaking to small crowds of potential supporters. When not on the road, he would be at Queen's Park fighting for scarce media attention. Behind the scenes, he would have to manage a 28-member caucus that includes five veteran MPPs who competed against him for the party's top job. In his spare time, he would have to steer the rebuilding of a party that, after four straight election losses, is deeply in debt.

If Mr. Ford led the Tories to victory in the 2018 provincial election, his job would get more glamorous. But it would also get even more all-encompassing, with even less ability to come and go as he pleased. Based on his brief stint at City Hall, that doesn't necessarily sound like his dream job.

How much of a provincewide organization can he build?

Mr. Ford might be able to sign up thousands of supporters in the areas of Etobicoke and Scarborough that strongly supported his mayoral bid. But that wouldn't get him all that far, because leadership votes will be weighted so every riding counts equally.

While his brand might translate well into some of the Greater Toronto Area's outer suburbs, where he'd be competing primarily with erstwhile deputy leader Christine Elliott and federal MP Patrick Brown, he would also need to make some inroads in eastern, southwestern and northern Ontario – the stomping grounds of candidates Lisa MacLeod, Monte McNaughton and Vic Fedeli, respectively.

With PC membership ranks very thin to start the campaign, and other candidates hardly setting the race on fire, there would certainly be opportunity for Mr. Ford to compete. But away from his familiar turf, he would need to quickly enlist strong on-the-ground organizers to help.

How much more money is he willing to spend?

To attract those organizers, in a party in which he currently has limited relationships, Mr. Ford would have to pay decent money. Of all the candidates, he might be the one who most needs to spend the $1.25-million limit.

Mr. Ford is not known to have a particularly strong fundraising network; a leadership run, like his mayoral campaign, might have to be largely self-financed. Even with his family's fortune, there may only be so much money Mr. Ford wants to invest in his political ambitions.

Is he willing and able to play nice?

It's very difficult for any candidate to get a majority of first-choice votes in the preferential-balloting system the Tories are using. So the process requires contenders to curry favour with opponents and their supporters, in the hope of getting second- and third-choice votes.

As Mr. Ford demonstrated this week, when he said none of the other candidates would be able to win against Premier Kathleen Wynne, magnanimity does not come naturally to him. Among his other calculations, he should consider whether he's capable of keeping his impulses in check.