I'm much more pessimistic about Kennedy siding with us then Roberts for a few reasons.
1) Kennedy is 76, Roberts is 57, age is a strong indicator of support for gay rights, demographically someone like Roberts is more likely to support it then Kennedy. Kennedy has also gotten more conservative over the last decade, another reason to think he won't side with us.
2) Think long term, like Justice Roberts did in the ACA ruling. Assume the worst happens and we lose both cases, what's the worst outcome we could expect?
2A) On Prop H8 we put it back on the ballot in 2014, and VERY likely win, overturning the courts ruling. We could have won in 2012 if we put it on the ballot.
2B1) On DOMA, the court upholds the whole law as constitutional. Congress starts to push more strongly to repeal DOMA as gay rights/marriage support clearly continues to grow. Give it enough time, democrats control both houses of congress and overturn it. We might not even need full control of the government, we won gay marriage in New York with a republican controlled senate, and I could see a republican president beyond 2016 fear for the party's long term demographic success and their reelection in 2020 that they have to support a repeal of DOMA. Plus, lower courts will likely continue assault different parts of DOMA, forcing the supreme court to almost certainly take up the DOMA case again.
3) Because of 2), if you're Justice Roberts, do you want to preside over a major civil rights court ruling, only to see your ruling overturned in the next decade (either by being outvoted in the court in later years, or by the legislature undoing your ruling)? I don't think he does.
4) Roberts has been pro-business, and some businesses have been urging the Supreme Court to overturn DOMA in order to get a national standard for marriage that's consistent across state lines, to make it easier to plan/run businesses that operate in multiple states.
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