Agreed. We do it because we enjoy it, but comparison across generations is a very inexact science, arguably even a pointless pursuit.
Ultimately, when we look for the greatest, we look for who succeeded against their contemporaries most consistently. While, as you note, it's about more than trophies, what all the super-greats have in common is excellence in the high pressure situations at the majors. By generation, Greenleaf dominated his peers the most, then it was Mosconi, then Lassiter, then Sigel. More recently, it has been Shane and now it is Josh. These are the players that have mass-produced titles at the majors, especially at World Championship events.
In the end, there's no real way to compare a Filler to a Sigel. Each mass-produced major titles against the players he faced and has a resume that is mind-blowing. Best is to just appreciate both of them for what they achieved.