As I've said time and time again, I think the title matters if the guy is what we fans consider a "wrestler". When CM Punk won the title at Money in the Bank 2011, it was an accomplishment for the IWC and the smart fans with the idea that, NOW this title is legit because one of the best wrestlers in the world has it.
There's instant credibility in those type of guys breaking the mold and holding the strap for a given amount of time. We know it's just a prop when Orton or Cena win it because, fuck, those guys have each won it 10 plus times. For a guy like Punk or Bryan, it's still something different and special because we the fans are smart enough to know Vince would prefer these guys not sniff the top of his company.
There's some pleasure in seeing a guy you use to watch in smoky gyms with 100 other people ascend to the top of a billion dollar wrestling company. When that's constantly taken away from you or swerved away from you, eventually you just kind of say "Fuck it" and yeah, the title as you mentioned becomes meaningless even when the guy you've been rooting for for 10-15 years gets it.