People who need to recoup their cost from Ang Pows usually lose money. Those who are prepared to write off the entire $50k usually make money.
The wedding couple are crap for spending above their means. Nowadays, high-end weddings mostly lose money. its expected. how to possibly recoup? unless you dam CB and invite only your rich frens and relatives. even then, I had rich relatives and frens who gave $50 per pax. rich also can be stingy. Furthermore, the groom has to "give" tables to the bride's family. Net loss for me was $10k but it was expected. anyway its a once in a lifetime thing. whats most important is that everyone went home happy.
The friends were also cheapskate for giving $100 only. so what if they are in debt? in sg, almost everyone is in debt. now the whole world knows that they are cheapskate and have no money.
personally, I dislike going to wedding dinners. have to give money and sit with a bunch of ppl I dunno, and still hafta make small talk. waste time. I rather give $100 ang bao, dun go, stay at home and play with my dog. at least, I dun hafta make meaningless small talk.