it was actually not too bad, it was colder than we would have liked. the last day we where there the temperature was near freezing in the morning. but all in all a positive experience.
we had everything arranged ahead of time. we had arranged an airport greeter guide us through all the airports at each of our stops so we didn't get lost, so bonus

when we checked in we asked for a tag to be attached to our wheelchair and a double stroller we where using for "gate delivery". it's something anybody can request. we early boarded... we rolled all of our stuff right to the door of the plane. very pain free.
my wife was "randomly" selected for additional screening at US customs in Toronto. And by random I mean there where several S's printed on the corner of the boarding ticket. so if you find "SSSS" on the corner of your boading pass... get your bum ready.

there was no real crazy security or anything, basic metal detector thing. push your carry-on junk through the machine. excuse us while we bombard your laptop with x-rays...should be good. the security had a separate lane for disabled, so it's a relatively short wait time.
while waiting to leave Florida at the end of the trip some dude got "sick" i guess and couldn't fly... had to wait for an hour while they dug his luggage out of the plane. coughterroristbombplotcough.

but i'd have to say the airport greeter that accompanied us through the airports was a godsend, it would have taken us hours to try and navigate through where we needed to be. at one point in Toronto we took some short cuts through some "airport staff only" doors... probably shaved 20 minutes off of our walking.