Two long questions...
Although you recently said you think Roman Reigns will win the Rumble, how much do you agree with the notion that Daniel Bryan "needs" to win the Rumble (and win the title back at 'Mania) to be established as a top guy? I can understand (many) fans wanting him to get his title back at 'Mania but think he's already popular enough that winning the Rumble wouldn't be as helpful to him in the crowd's eyes as someone like Reigns or Rollins or even Rusev, none of whom are generally viewed as main eventers. And WWE reluctantly booking Bryan to win the Rumble isn't going to make corporate believe in him any more than 'Mania last year did.
Additionally, while Bryan winning back the title he never lost (even if it's not from the person who took it from him) is a good story, how much confidence do you have in WWE Creative telling that story given how badly they've booked the three biggest babyfaces in Bryan's absence: Cena (hero avenging Summerslam slaughter who gets into a #1 Contender's match by losing and is impotent when his allies are fired), Reigns (up-and-comer establishing himself by beating the big bad champ who is given Looney Tunes and fairy tale promos), and Ambrose (psychotic hellbent on revenge becoming a prop comic who loses to holograms and exploding TVs)?
I don't think he NEEDS to win it as far as his character or standing or whatever goes. I think that WWE kind of owes it to the fanbase as an apology for last year and it would go a long way towards building goodwill. Really, if he's booked in a strong Wrestlemania program (hint: NOT KANE) with a direction that makes fans get invested in him again, he'll be OK. Now, that being said, if they didn't want him winning the Rumble, he shouldn't be in it. It's only going to hurt Reigns just by virtue of not being Daniel Bryan.
Like, Bryan can be the guy to dethrone Rusev and that's an easy one to book and build sympathy and such. The Brock match is of course the fireworks factory that we're unfortunately never going to arrive at, but that's another one that literally books itself. It doesn't HAVE to be the story of "Bryan wins the Rumble and then gets the title", but it just happens that it's the only story they know how to book this time of year and the only one they really get behind.