I think your first paragraph there was a little over the top.

Yes, some execs get paid too much, and I'm sure there are plenty of people at M$ that don't get paid enough for what they're doing. I can't do anything about that.
As far as debt, pretty much every company has debt. It's not always a bad thing. But if you're putting off profits long enough, even if you have a good amount of cash on hand you can't expect to go on too long without profits coming in. I'm not even going to pretend to know M$'s financial situation, so there's not much more I can say about that.
Most students already get ridiculous discounts on OSs. I myself didn't go to college but most of the people I know that did could go to their school bookstore and buy Win XP Pro for under $30.
As far as a family discount it just seems like something that's going to be hard to do. You have some families that have one kid and 3 computers, then you'll have families with 3 kids and 8 computers. I just don't see any good way to do something like that besides buying licencing in semi-bulk. That would be done more at the retail level though.
And most people are giong to get the OS with their computer anyway. If you want to upgrade an old computer, buy the upgrade, it's alot cheaper than a full retail version.
People like me
have to pay for it because people like you steal it. It's common sense that if you have something that should be sold for $100, but 30% of possible clients steal it, you're going to have to raise the price to compensate. As far as M$ making a version that can't be pirated, that's just a bad argument. They should have to if people weren't immoral and stealing in the first place. Since people aren't they have to work hard to put that in place, but it's impossible to make a perfect system. Something can always be cracked, there is no perfect security.
And it honestly makes no difference to me either because I get all my M$ licensing through work. I haven't had to pay for a copy of Windows in over 5 years. I do feel bad for the people that have to pay more because of all the thieves out there though.

If you're on my side you should back me up. If not, stick to your original idea.
Most of those kind of discounts would be done at a retail level. I don't know if M$ would actually setup a family pack or anything like that at their licensing level. Who knows though, the way the economy has been we could see a shift. Technet would be a great idea for alot of people if they use alot of M$ products, but that $350 is yearly if you want access to new stuff that's not on your existing subscription.
I don't think M$ does everything perfectly, but we don't either. The OS wouldn't be as expensive if so many people weren't pirating it, that's a fact. In addition to making up for losses associated with pirating they also have to pay people to research new ways to make it harder for Windows to be pirated, which again adds costs. Yes M$ still manages to make a profit, but if they weren't we wouldn't be seeing a new OS very often.
I think I've gotten my opinion out sufficiently so I'll stop with the massively long posts now.