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I'm not sure whether they'll play with Jericho as heel or face, I think he could work as either.
The fans seemed to be completely behind him upon his return, and a face/face feud with Punk may be more interesting than a conventional Heel Vs Face angle.

I really can't stand Punk though. He comes across as really arrogant and obnoxious, and I skip forward whenever he sits down in the ring to cut another 10-15 minute promo about how he is the catalyst of change, when in reality he's only holding the championship because Cena is embroiled in other feuds and Mysterio's injured.

As for his feud with Johnny Lauranitis, I prefer the Interim GM. He greatly amuses me every time he shows up to announce his full job title and to troll the crowd by telling them he knows exactly what they want and booking the opposite.
When you think in retrospect, of all the animosity Punk has towards him, until recently, it has just been based on Punk being a loud mouthed twat and signalling out Johnny for bullying, despite Johnny being nothing but impartial.

I'm pretty confident Bryan will retain at the Rumble. It is clear they have no long term plans for either Henry or Big Show, or they would not have had both men drop the title when they did.
In my mind, Bryan hasn't had his truly defining heel moment yet, which I think will come at the Rumble, where we can all sit up and say: Yes, this is the moment where Bryan is officially heel.

However, if Barrett wins the Rumble expect Bryan to drop the title before Wrestlemania. A heel Vs. Heel feud would be rather pointless. If Sheamus or Orton wins, I see Barrett taking the title at Elimination Chamber, as Bryan just doesn't look like a strong enough champion to go into Wrestlemania as the guy to beat.

On a side note, when Bryan turns completely heel, does Cole have to go back on everything he said, and start supporting the guy?

I heard that Regal wanted a match too, perhaps if Jericho wins the Rumble, they'll have a No.1 Contender elimination chamber match for Smackdown, similar to what they did for Raw last year and have Bryan go over Regal, who isn't exactly a legitimate challenger any more, but would still get a good match out of Bryan.

On the subject of the Swag man, I think he is in his correct position. To me, he does not have the main event potential, as was proven with his horrendous WHC title reign.
He's got a good look, despite looking like an oversized child and is a good in-ring worker, however, his lack of promo skills (I think he may have a lisp too) as well as his never changing persona holds him back.

However you have to have midcarders in a wrestling promotion, and that is where he thrives, he should do well as U.S. Champion.
Not everybody needs to be a top guy and have championships slapped on him. Mr Ass and Road Dogg were always over, but nobody demanded they be pushed as WWF Champions.
I'm assuming as the WWE claimed Ryder had broken his back, that he won't be back to claim his rematch anytime soon.
I forsee a possible Kingston/Swagger feud or perhaps a feud with Brodus Clay.

Speaking of Kingston, I think we'll see a return to solo action for him again, as Evan Bourne got himself suspended, AGAIN, for violation of the wellness policy.
His current ban will keep him off TV for 60 days, and I don't see him returning after that.
They obviously had faith in him and Kofi, as they let them keep the belts following his last suspension, but this time, they didn't even feign injury to write him off TV, and had Airboom drop the titles at a house show.

On a final note, I find myself looking forward to the Rumble with great excitement, I've really enjoyed the Kane/Cena feud, and am interested to see how it plays out, I always enjoy Ziggler in the ring, and it'll be good to see him get a 20-25 PPV main event slot.
Also, the Rumble itself looks like it is going to be great.
I think it's a good thing that they've knocked it back down to 30 guys, in my opinion 40 competitors was just a big mistake.
So, yeah. Looking forward to the Rumble and the unpredictably it brings.