A company that never has one of the qualifying events is likely to be an extreme corner case. So an investor could end up holding a safe for a while, but for the vast majority of companies, there will be a financing or a merger / acquisition at some (or an IPO).

Correct - the notes had this feature too, except that rather than shadow preferred, it was the preferred / common "unit" concept. The net result was the same.

Great question. Re: the implied valuation of the company, I don't believe it will be different from the notes. The safe will convert to preferred stock, and while the price of the preferred stock certainly affects the price of the common, I think it would be hard to say that a prospective valuation for an event in the future increases immediately increases the value of the common stock.

I guess I'm not asking about the implied cap from the future conversion into preferred, but the EV stemming from the mere ownership of, say, a million dollars by the company. We use restricted stock that vests by lapsing a right to repurchase, since it's cheaper for the employee (no cost associated with the option itself) and it starts the long term cap gains clock right away. This makes them a direct shareholder, though, and if the only stock outstanding in the early days is common, it seems like the cash-related EV would have to be attributed to it, right?