I think Tom Petty, for the most part, found a great formula and stuck to it. It's produced a great catalogue of greatest hits that everyone seems to like. Unlike an artist like Bob Dylan, for instance, who went through some pretty goofy phases and alienated a lot of people. Petty's shows were more greatest hits showcases than anything (except I'm pretty sure he was doing Wild Flowers in its entirely during the last tour), but that worked, because it seems like almost everyone is at least a casual Tom Petty fan.
It also seems like Tom Petty's most popular songs are also his best, which isn't always common with rockers. You mentioned Springsteen, and I don't think many casual rock radio listeners have ever heard a lot of his best songs (Backstreets, Lost in the Flood, Paradise, Youngstown, Long Walk Home, Moonlight Motel, etc... shoot, even more popular ones like Badlands), because the songs that get the most frequent radio play are, quite frankly, not his best (other than when the classic rock stations play something like Born to Run). But that doesn't seem to be the case with Tom Petty. You don't need to delve very deep to be a fan; you can just stick to the radio hits and still really like the guy.
I don't really put him on the same level as the aforementioned Dylan and Springsteen (they both have outtakes that could have been career highlights for Rock and Roll Hall of Fame-caliber artists), but he's damn solid and a guy that almost no one dislikes.
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