7.1: It is debt.
The fact that the payments are fixed and tax-deductible make it debt. The fact that the holders of the security have to wait for other debt holders makes it more like unsecured debt.
7.2: The venture capitalist who is invested only in software businesses
The fact that this venture capitalist is not diversified will result in him demanding a return for all of the risk in the sector, including some of the risk that is diversifiable.
7.3: The venture capitalist with a higher required rate of return
The only way to earn the higher return is to get a disproportionate share of the ownership.
The warrant prices are high because they should be high. It is only if the market is over estimating the variance that warrant issues will be justified.
There might still be scenarios (such as project financing, where the firm might want to convey propreitary information to the lender) where bank debt is superior.
The short term rates are lower than long term rates because of differences in expected inflation and a liquidity premium (for risk). Neither is a sign of inefficiency and neither can be exploited to lower the cost of borrowing.
The convertible bond yields are lower because they include a valuable option (the conversion option). Unless this option is mispriced, convertible bonds are not cheaper than equity.
Preferred stock shares as many characteristics with debt (no voting power, fixed payments) as it does with equity. It is closest to non-tax deductible debt.
There is no tax benefit from interest expenses because of the net operating loss carry forward. Next year it will drop to 4.8%.
7.10: Conservatively financed, publicly traded firms with a wide and diverse stock holding
Private firm owners invest their own money. Public companies with activist stockholders have another mechanism for maintaining discipline.
7.11: Airplane manufacturer, High-tech company, Grocery store
Airplane manufacturers have large implicit bankruptcy costs, because their contracts with buyers tend to be very long term. High-tech firms have a high variance in operating income, leading to a higher probability of default. Grocery stores have low variance in income and low bankruptcy costs.
The risk that they will not get these cash flows, even if they hold until maturity, has increased and they are not being compensated for this risk.
7.13: Microsoft's management
It has a much better track record of managing your money, and has the potential to earn higher returns with that money.
7.14: In much more financial trouble than the average firm
Why else would they be scraping the bottom of the barrel and issuing convertible preferred (the least preferred option)