I think your focus on "losing money" and the exact "high" (risk) wording has made you miss out on how this system is supposed to be used. Is there a high risk of losing money with every purchased account? Even theymos argued against it ("Individual cases can be debated on their merits, though"), and said it was still appropriate use of the system.
When you support this flag you're saying that there is a high risk of losing money dealing with this particular user (not in some hypothetical account sale scenario) and that the referenced thread contains evidence.
I will oppose the flag for now because I "believe that it is at least partially false".
