Playing chess for money also puts chess into category of gambling. Society wouldn't view chess as an educational game and instead will view it as gambling. Parents will discourage their kids from playing. In history chess for money also made some governments ban chess in their countries or create laws limiting it. When Russia had casinos before 1917 they had chess rooms inside the casino. Botvinnik was introduced to chess by sneaking into a casino as a little kid and he got into trouble with his parents.
In some Muslim countries like Iran chess is criticized by clerics and imams. They even try to get government to ban chess not just because some people gamble, but also because they believe it makes Muslims angry and too adversarial toward each other.
Anyway. It's a bad idea to play chess for money. Especially with a stranger. It's not even because he can win your money but also because he can be a street thug or criminal who will take your money by force whether you lose or win.
OTB
For example friend friend you walked pass playing chess, he asked you wana play for $, would you chicken out or be like how much? Straight to business
Or any other scenario , you don't know someone and their level how much would you play for and just one game or..?