Nobody receives a ringing endorsement from Daley. His general silence on Rahm's candidacy versus his dings at the other candidates is about as close as anyone has come.
The Daley - Obama relationship can't be that bad since Obama has relied heavily on chicagoans who are connected and Bill Daley moves up to replace Rahm.
What most people don't seem to understand is that the "Chicago Machine" isn't a single monolithic construct. Certain parts have their own, possibly quite different, agendas.
yes, the south is very different form the north in Chicago politics, and Obama alienated them both. As well as the various unions and districts etc...
It was a long road for all of that, though. Jackson/Sharpton were firmly opposed to Obama during and after his race with Bobby Rush. he was more of the progressive candidate, while Rush was the "keep us blacks where we are and our politics where they have always been" candidate--like Jackson and Sharpton have always been. They outright resented Obama for trying to be the black politician with a message very different than their civil-rights era foundation.
Daley was not really a fan of Obama during the 04 campaign, and he did not immediately endorse him during the presidential campaign. IIRC, he was always a Hillary guy.
there was a super excellent New yorker article a few years ago on Obama's political career with all of the dirty details that you can expect. Also a really well-done Frontline documentary. He pretty much alienated himself by not seeking the endorsements that he was "expected to seek" as an up-and-coming Chicago politician. Tons and tons of resentment from the machine(s). He really is the most un-Chicago politician to come out of the city.