It has been mentioned a couple of times, but definitely check the size. Westjet and Air Canada have slightly different maximum sizes. I have a cheaper small suitcase (that I don't use) that is advertised as being carry-on size, but there is no way that it would fit in the sizing device. The manufacturers and retailers don't care - the airline might.
I would actually guess that the majority of those little suitcases would be too big if the airline wanted to get sticky about it.
I would also get something that would also withstand checking, and not so deluxe that you'd be upset if it got damaged. Some days I'm just not in the mood to compete for overhead space, including joining the boarding line super early. People always did that, yes, but even more so now that they're competing for space. Depending where I'm arriving and whether I'm in a rush (usually I'm not), I'll prepare for carry-on but occasionally check it when I get to the airport as my company includes one on the fare. Or volunteer to be a free gate checker when the announcement inevitably comes. If the flight isn't full and they don't need gate checkers, even better.
The speed advantage of carry-on is real, but when you're landing in Saskatoon/Winnipeg/etc. at 8pm on a Sunday night, by the time you've emptied your bladder, the bags are usually tumbling down to the carousel anyway.
Also, I am a big fan of packing cubes. Nothing fancy or the ones where you can suck the air out (but I can see the advantages of those too) - just simple packing cubes with zippers. It makes packing so much easier, and it keeps everything tidy when you're away. Whether you're going overseas for a few weeks with a checked bag, or something shorter with carry-on only, I love packing cubes.
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