I looks like Ethos Capital would have had to make at least $100 per domain to recover the cost of buying the .org registry, never mind making a profit. I wonder how much of a profit they were aiming for and how quickly they planned on making that profit...
Exactly, a non profit making X money per year is harder for insiders to profit from. However, setup a sale to the company of your choice and suddenly you can profit handsomely.
From an investment standpoint it can make sense to convert a slow but reliable income stream into a big chunk of cash that you can invest in riskier assets with higher returns.
The math is different for non profits as they are excluded form income taxes where a for profit company is going to be heavily discounting the value of that income stream.
Thus, it would generally be better for the non profit to simply take a loan out based on the income stream and invest that.