In certain very LCOL urban areas around NYC and Philadelphia, we have individuals with tens of millions of dollars of property spread out among ~$150k buildings.
They inspect their portfolio with armed bodyguards, and they very often own other businesses in the same neighborhoods that throw off money in small but regular amounts: laundromats, bars, clubs.
An an interesting aside, these individuals are almost all involved with close-knit religious groups to which they contribute great deals of capital.