I'm not surprised you were struggling with these; they are full of jargon and inside references. Anyway, let's get started and I'm sure others will chime in too so you get a better picture.
1. You could say it came with caveats, or considerations to bear in mind when you call it a victory. (An asterisk * would refer to some qualifying footnote.)
2. Not here, no. It's probably from someone who doesn't know what he is talking about. A "statistical tie" would be if you repeated the experiment (here, the election) a number of times and you found the number of times Clinton won was within a certain margin, statistically defined, of the number of times Sanders won.
3. A "truther" is someone who (oddly enough when you think about it) denies the truth of some official or commonly held position, in this case the outcome of the election. They will often have a "conspiracy theory" about what "really" happened. So the "flip truthers" here may believe that the coin tosses (which is apparently how they run some elections in Iowa) were biased to Clinton and fixed the results. Probably again, not a statistician talking, since the probability of 6 heads coming up given you know, well, 6 heads came up, is different from that of 6 as-yet unflipped coins coming up heads.
4. In this case, yes.
5. Wild cards are playing cards in a deck that may take the value of any of the others in certain games. So you don't know their value beforehand. Here, they are trying to say they have no idea about the human resources. When they say "huge", they mean the uncertainty is huge. Of course, they could have just said that -- no playing cards are bigger than any others in the deck, so the image isn't that helpful.