I just had an interesting thought...
What if Ann is the same call girl Brenda Strong played on the old show?
Think about it.
Cliff hooked up with said call girl in the final season of the show (1990-1991) when he had, ostensibly, been dumped by Liz Adams.
It's unlikely Bobby would have met the Brenda Strong character then, but also very likely that Cliff would have forgotten all about her. Never mind the fact that Harris Ryland is just sleazy enough to have probably hooked up with her at the time too.
How fucked up would it be if Emma is really Cliff's
daughter, and Ann played Harris into marrying her? Or, perhaps she really is Harris' daughter.
It would also explain why Judith despises Ann so much, and Emma's age works out almost perfectly for it as well.
I don't know that this isn't too farfetched an idea, but it's fun to think about!