We tried Southwest for the first time last month...flew non-stop from BUF to Tampa for $435.xxUSD for 4 r/t tickets.
Our flight was a little past 7 AM in the morning, so we stayed at the Homewood Suites the night before and left our car there for the duration of the trip. Took the hotel shuttle to the airport and arrived just over an hour before the flight. Security was quick and we had plenty of time before boarding - but not TOO much time. Our kids are 5 & 2, and all that time spent waiting for a flight can be brutal, but the Buffalo airport has a couple of small play areas for the little ones that help to pass the time.
DH absolutely LOVED the experience of flying from Buffalo. He doesn't mind the drive, and he was even fine with driving home directly after our return flight even though we didn't get in until after 9 PM and it was after 10 by the time we got to our car. Crossing the border was a breeze at that time of day
I am one of those people who worry about weather conditions. A few weeks back Westjet was offering non-stop flights from Hamilton to Orlando for $99 pp each way, the total came to just under $1200 for the four of us, which is not bad. However, there was only one flight per week to MCO and one flight per week returning, so I was concerned about delays/cancellations and didn't book.
But on Christmas Eve I got a great ding! fare on SW so in February the four of us are flying BUF-MCO non-stop, return, for a grand total of - are you ready for this -$373.xxUSD!!!

Again, I'm concerned about the weather, but SW has frequent flights to/from Orlando, and we're allowing an extra day on either side of the trip for driving.
So for us the drive to Buffalo is definitely worth the cost savings.
We plan on taking a cruise with my in-laws in the spring, and when travelling with them we will likely fly from Pearson because of my FIL's medical condition. We will be paying through the nose for the convenience, though..last week the cheapest flight I could find was $519CAD pp. We're going in April, though, when I believe flights tend to be more expensive.