conservatives just aren't very good at budgeting, huh?
i think the issue here is the time requirement. he appears to be arguing that he shouldn't go to jail over unpaid fines - which is what is about to happen - rather than that he should be allowed to pay the fines down personally. the payment option being presented is just a scheme to avoid jail time.
and, debtors' prisons would be a pretty unconstitutional - and pretty uncanadian - concept, for sure.
it follows that the judge can skip the issue discussed in the article by striking down the criminality around indebtedness, which is the more direct question. but, i might suggest that it is overstepping it's bounds by striking down the law, in the absence of a clearer breach - merely stating "but, i'm in debt and i can't pay it off" isn't a demonstration of a rights restriction so much as it is a demonstration of mr. leary's fiscal incompetence, and perhaps why it is that he was unsuccessful as a candidate. mr. o'leary made those choices.
there is a valid point, here - he shouldn't go to jail over this. that's too much. he should just be forced to raise the money, until he succeeds in paying it off - or until the parliament decides to change the law.
https://www.cbc.ca/news/politics/powerandpolitics/pnp-tasker-oleary-suing-elections-canada-1.4905684