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.
I've said this from the get-go as well, this angle can be done with any wrestler on the roster. This shitshow of a "best for business" storyline could have been done with The Miz to largely the same effect. Daniel Bryan deserves better because he is better. He's earned the chance to have a solid run at the top of the company ala CM Punk/Heyman last year. Instead, he's an accessory to a larger storyline. Granted, he's still been way over and good for him, I'm really glad but I can't help but wonder if one day people will just say "This guy is a fucking geek" and stop screaming Yes. It hasn't happened yet, but I'm not sure how often you can make him the fodder before it happens or before management decides he needs to put a suit on and work as an analyst.
With any of these "internet darlings", you feel like you're on borrowed time with them at the top of the company so to have 5 months of him being in main event is great, but the matches haven't been particularly good because there's so much bullshit in and around them. He was having way better matches with the same guys on TV months ago.