phil getting fucked = funny.
the method isn't important, only the outcome
I agree with you in general but there are some caveats.
Don't plan it here, don't talk about it here, don't come here to brag about it. If you're trolling or screwing with someone because you think it's fun or funny, that's fine, but doing it for (fuck, i hate this term) "clout" then you are a retard orders of magnitude larger than the lolcow you are fucking with.
Don't involve other people. Phil's parents could argueably be somewhat responsible for what a retard he is, but that isn't a reason to try to fuck with them. Phil's neighbors didn't choose to live next to his combination horse-pig-stable. Trying to screw with anyone besides the lolcow themselves is profoundly retarded and unjustifiable.
I'm sure there's more but I'm too tired to outline them. Bottom line, yeah, people finding clever/funny/interesting ways to screw with a lolcow can be entertaining, but 99.9% of the attempts are not.
A good example of this is the "troll tipping". In an overwhelming majority of the cases where people try to, they fail, get mogged by Phil, get ignored. In the end all they've done is given him a dollar or two and made themselves look like a retard. On an exceptionally rare occasion someone can get him to go into an hour-long rant about something, get him to have a meltdown, elicit some new piece of lore, or get some other kind of interesting or funny reaction that I would say is worth the dollar or two. The issue with it is that everyone thinks they are that guy, and they are not. It's just easier to say that no one should ever try, and that it's never funny because in almost every case you'd be right.