2016 - Democrats take back the Senate, winning NH, PA, OH, IL, WI, NC, FL, MO, maybe IA if Grassley dies or retires or something.
Hillary wins the Presidency with a large Electoral College margin, solidifying the theory that the GOP is becoming uncompetitive for the White House. Hopefully Breyer and Ginsburg retire in 2017 or 2018.
Hillary makes for a better fit with the public for Democrats to win seats in the House. Losing votes in city centers but making big gains in smaller towns and suburbs, basically spreading the Democrat vote out geographically, which I think is the primary problem the Democrats face in the House elections
2018 - the Democrats almost inevitably will face loses in the Senate, maybe losing the majority. The good part though is a lot of governor races will become competitive and the Democrats might make real good gains there similar to how the GOP did in 1986. That will make it much easier on them for redistricting in 2020.
2020 - Who the heck knows, I'd be slightly willing to bet Hillary wins reelection though, barring some crazy unforeseen events.
That's still only a 289 - 249 EC win....hardly what I'd call a "comfortable victory"