It takes decades for a population center to empty. Plenty of time to recoup an investment. If he starts with low hanging fruit, like transit between deadlocked

It takes decades for a population center to empty. Plenty of time to recoup an investment. If he starts with low hanging fruit, like transit between deadlocked parts of LA he'll be making money. Maybe eventually he gets down into boondoggle territory, but I don't see why that should be a concern. As part of a larger fund, a few boondoggles are no problem—learning experiences.