Late, I know, but here's some context to the Sanders-related chimp out that I don't think was mentioned.
He donated money to Sanders because the perception at the time (still is, I guess among Sanders supporters) is that "Sanders can't be bought UNLIKE HITLERY KKKLINTON sperg spergity sperg", so Shkreli donated a bunch of money to Sanders to prove he could be bought. The Sanders camp donated it to a charity. Initially Shkreli gloated that since he hadn't returned the money to him, he had still been bought. Then he challenged Sanders to a debate on healthcare. Then he concerned trolled that he just might have to vote for a Republican if Sanders was going to treat him this way

. Then when he realized none of those things were making people as assblasted as he'd hoped, he pretended to chimp out and punch walls. It was a total ruse.
Pretty sure this wasn't mentioned either: He was also bffs with Geoff Rickly (former singer of the post-hardcore band Thursday) and was the silent partner/primary financeer behind Rickly's indie record label, Collect Records. When the initial shit about Shkreli raising prices on daraprim by 4000% or whatever happened, it was discovered that he was behind financing the label. Several bands on the label quit, more threatened to, and Rickly was dumbfounded that Shkreli was being an asshole (having previously seen him give tons of money to charity) but severed relations with him anyway to keep the label from imploding. It then turned out that without Shkreli's shekels, the label didn't have enough money to continue operating. IIRC, someone asked Shkreli about this whole debacle and his response was basically some variation of "lol".
Anyway, as most people are aware at this point, the dude is basically king troll and any chimping he does has to be taken with a huge grain of salt. He deletes tweets when certain trolling angles don't pan out, keeping only those that cause the most salt from the people reading it. He's 100% self aware. His persona is 50% comic book super villain and 50% a white version of those "Rich Nigga Shit" videos Soulja Boi used to do.
While he's definitely an asshole and also a criminal, I'm on the fence about him being a lolcow. Any milk from him is probably tainted by him being in on the joke. He's just a rich kid who likes to fuck with people and create chaos. I agree with whoever said he'd probably fit in well enough here. As the old saying goes, "There but for the grace of God, 40 million dollars and a desire to fuck with AIDS patients, go I.'