Am I the jerk for dreading visits to my in-laws in the Philippines because I'm expected to pay for my wife's friends and family too? (AITA)

No.

Five years is a really long time. Your wife needs to see her family and you need to grit your teeth and go along with it. Yeah, you're going to have to spend some money one way or another, but that's just what comes with marrying a Filipina. Still, the demands, the guilt-tripping, and all the sob stories that come flying in while you're there are 100% on your wife to handle. They won't ask you, they'll ask her to give them money, to "lend" them money, or whatever. Do this. On the first day you arrive, gather the whole clan for a big dinner, but don't go to a restaurant — throw the party at her parents' house or a relative's house with plenty of room. That's what we do now, and it's way better and cheaper. The family probably prefers it to going out to a restaurant anyway. Usually everyone likes to cook, and cooking together is a big social event they enjoy. It'll cost around $60, or maybe $100 total if you buy a whole pig, but you'll make a huge amount of food and eat it for the next 3 to 4 days. After that, stay there at most 4 days, then slip away and travel on your own to another island or somewhere else in the Philippines. Telling the people who want to tag along that they can't come is your wife's job — if she does it well they won't get angry, and they might get angry, but oh well. Good luck.

This does actually happen, but it varies from family to family. The pressure on the "well-off" child is real. Talk with your wife, and if you decide to go, make a proper plan that you both agree on. And make your expectations clear to her side of the family from day one. I don't buy at all the idea of covering the family's friends too so her father can play king of the barangay for a day.

Yeah, you're a total jerk. That sounds less like "expectations" and more like just assuming things. To borrow my teacher's line, you know what happens when you assume — it makes an **ass** out of **u** and **me**. Is buying one $30–50 meal at some neighborhood restaurant going to bankrupt you? If you weren't going to see the family, why did you get married?