I think that beyond personal satisfaction of finishing a list on a "fine" peak, there are two real things to keep in mind when planning:
a) how much will bad weather affect the hike? For example, saving a Presidential for your final winter peak sounds great, until week after week you can't get up there due to bad weather.
2) who is your accompaniment? Will you be joined by friends? Some peaks simply lend themselves better to group hikes, especially if some are less skilled hikers, or not even hikers at all.
For example, some people save Isolation as it is a beautiful, remote peak. But then they might have to consider if their friends can do the mileage, or if the weather is iffy, if their friends (or themselves!) want to spend that much time out in the heat/rain/blinding snow.
This is not to suggest that you should finish all your lists on Cannon. I'm simply offering that there can be real reasons to plan ahead.