Why do so many Westerners feel the need to over-analyze Filipinos?

Western countries like Canada are mostly First World countries where things work. That's why everyone wants to immigrate to the West, and there's almost nothing to complain about. The Philippines is a Third World country with lots of problems. That's why it stands out much more and is more irritating to someone coming from the First World.

Filipinos analyze foreigners way more than you'd think.

The irony is that people accuse others of having a superiority complex while thinking they can pin down those people's motives and psychological problems from a few posts. Discussing Filipino culture isn't the same as claiming to know Filipinos better than Filipinos do. You can disagree with someone's observations, but not answering the actual argument and blaming hatred or insecurity is the very same behavior you're criticizing. Living in a country doesn't automatically make your observations right, and being a foreigner doesn't automatically make them wrong.

Most of those posts aren't genuine. They're mostly the same people writing under multiple names. It's pretty much a hate and smear campaign aimed at the Philippines, and they react to their own posts. If you read them, almost all of them are written in the same voice. Then elitist, entitled expats jump in, agree, and comment, pushing them to the top. That said, I have to say I've met plenty of those expats in real life too. In person they really seem delusional. They use phrases like "I live like a king in my barangay." Because of one or two scams or one or two Filipinas they dated (who probably did their best but couldn't stand that person's delusions of grandeur), they generalize about an entire culture and an entire country, and now they judge the whole country by that. And I think a lot of them are actually just seriously homesick and don't want to admit it, or they can't go home, or don't have the money to, even though they're living like kings here.