My distant cousin managed to seduce a girl in a bar and she was so infatuated by him that her dad had to personally come and request him for marriage on his daughter's behalf. It just so happened that the dad was also a big shot businessman in the textile industry.

This seems like an obvious answer but looking good is not the only quality one needs for it. Not sure how "game" would reflect in interactions like these where the power dynamic tends to skew towards the woman as she holds financial dominance in the relationship.

If one is aiming for a "life on easy mode" as you put it, what would it take to charm a woman of a higher income group to provide for you? And is it really viable if you aren't that good looking in the first place? What's the Looks to Charisma ratio at play here? Feel free to discuss.

As a side note: He got a lavish wedding in Bahrain as part of the parcel. We had fun touring the Middle East