> I also enjoyed his trollish sense of humor.
I think that makes the title that much easier to understand. I'm an old-fuddy-duddy (for example, I say things like 'fuddy-duddy'), but to me there are two forms of trolling.
One where you're doing it to get their reaction and entertainment when they get it. I find this usually fun - the person doing it has fun, any audience has fun, and the person has that anguish-relief-joy cycle. When you do this to someone, you aren't gaining joy from the first emption your stoking, you get joy when it's found out and that emotion changes. The trolling itself is building anticipation. An example: My wife bought me a PalmPilot (back when those were a thing) but secretly took it out of the package to charge it, then gifted the surprisingly-not-much-lighter box to me. After my moment of feeling like I'd have to wait longer for my new toy (to try and return it) she revealed it fully-charged, and we had a laugh.
The second way is subtly different. The trolls are still poking at a person's emotions. They can SAY the target should get it and enjoy it ("relax, it's just a joke"), but really the goal is to entertain the troll and any audience. The targets of this trolling don't get a laugh. They get anxiety/hate/fear/dread/panic/anger or whatever, and the troll gains satisfaction from that, not from when that ends. Example: Posting political/moral thoughts that you don't have, but that are deliberately chosen to invoke outrage within the forum you are posting to, then moving on to the next once that's gotten enough reaction.
I'm obviously biased, but while I can appreciate the first kind, the second kind just seems to be increasing the misery in the world for a laugh. Laughs aren't so hard to get in other ways. Misery is miserable, by definition.
So if someone is described as a "troll" I tend to be leery rather than eager. When I encounter someone, it's very easy to find EITHER kind of trolling annoying. Perhaps because your brain is trying to fit people into a context/schema and trolling disrupts that. Brains don't tend to react well to that sort of thing. Known friends and family don't cause that reaction.
I don't know anything about Shkreli other than what I've read, but if you say "most hated man in America" and "trollish sense of humor", my instinct is to nod knowingly.