A helicopter hovering in one spot would be more conspicuous than a fixed-wing aircraft flying in circuits. After a while an observant person might become suspicious of a fixed-wing aircraft flying in circuits (as Doug Ford was) but most people would be completely oblivious. I think for these reasons the fixed wing aircraft is a better platform for police when conducting aerial surveillance.
I believe helicopters are also much, much more expensive to operate than a simple light prop plane, which I'm sure also figures into the discussion.
I agree that given the widespread nature of the current round of leaks, it does seem like something big is going to go down. One example: to put it charitably: the National Post, for example, does not have a strong track record of breaking news from within the police department. When they are running stories that cite a "police source" telling them that the mayor, personally, is under investigation, it probably goes down something like this:
Post reporter to TPS spokesman: "The Star is saying you have a plane flying around spying on the mayor because he's under investigation. Is that true?"
TPS spokesman: "On the record, no comment. Off the record: I wouldn't deny what the Star is reporting."
In other words, the police aren't making much effort to hide what they're doing. Which, in turn, suggests they largely have what they were looking for, because otherwise they would never compromise the secrecy of an investigation by being so open with the press.
Additionally, Doug's claim in today's Sun that the police are pursuing the agenda of a cabal of "elitists" seems like the beginning of the Fords' PR plan for when and if they are charged with something.
I may be wrong about this, since there have been other times--notably right after Mark Towhey's firing--when it seemed like the flood of leaks was leading to some huge reveal. But my hunch is that we are getting to zero hour for whatever is coming from TPS.