What will Obama do, and when will he do it?

The "what" is easy.  He will issue an executive order granting legal work and residency status for millions of undocumented Hispanic residents in the US who came here primarily during the Reagan, and both Bush presidencies (Clinton too, but the Democratic PR spin won't put much emphasis there).  The "when" is the issue at play.  The corporate media (both alleged liberal and Fox) seem to think he will do it sometime before the midterms.  This doesn't make such sense.  Issuing it prior to the midterms would make the situation for Democrats even more perilous.  It would not likely spike Hispanic turnout beyond what it already will be, yet it might spike turnout of the far right and push independents that are on the fence, or likely not to vote, into the arms of the reactionary Republican backlash.

He will do it after the midterms, when the maximum medium term (over the next two years) political benefits can be most easily realized.  Republicans are all but certain to take over the Senate anyway, but their hold on it can still be minimized to around 52 to 53 seats (a number easily turned around by down-ticket effects from a landslide JEB! loss in 2016), and the House is not likely to see a big swing towards a lot more Republicans since the GOP maximized its geographic and demographic potential there in 2010.  Doing it after the November election, and baiting the GOP after they are emboldened by a Senate takeover, yet still fearful about their long term Hispanic problem, into a panicked establishment push for JEB! to counter a simultaneous massive reaction by the nativist base in the House against the order is the political rationale for Obama's coming master stroke, and this will determine the timing of it.