The ORD-MSY route probably still uses TED 1-class planes on most of the daily flights - so e500s aren't able to be used.

ORD-IAH might be hard for a premier to upgrade using e500s - but having e500s in your account is never a bad thing.

Anytime I can find a flight to SFO for under $300 I take them, so I'd head out there.