First, I remember when people coming to pick one up could go right up to the arrival gate. In those days it was okay to have a bit more carry-on than one could handle, as family or friends could help carry it out of the airport upon arrival. In some ways that seemed faster than waiting for luggage to get to the carousels.
Then, after 9/11, getting through security became such a hassle it became better to try to stick everything inside one's check-in. That allowed one to jump through the process of getting aboard the plane without being so intrusively molested.
Now, of course, many airlines have begun charging $25 to check a bag. So, on short trips we try to get by with what can fit in the overhead bins.
A lot depends on the length of the journey but we have spent months traversing parts of Europe or Asia with just a backpack and one carry-on sized bag. Yet, this upcoming flight to Puerto Vallarta is going to be different. We have found our old, larger bags because WestJet allows one free piece of checked luggage when flying out of Vancouver directly into Mexico. As we are going to be gone for months, the things we are putting in are not typical.
We are going to be living there for a while, so we will buy a lot of what we need right there. Also, we must consider that many items are probably cheaper in pesos. Still there's the convenience factor to consider: sometimes it's easier to throw an item into the bag than go around looking for it upon arrival.
Things never stay the same.