I would percieve the situation having "$101,000 in the bank and owing $100,000" to have much more freedom than the situation of "debt free with $1,000 in the bank."
Been there --done both. But you fail to mention that being debt free allows more money to save towards that 100,000.
Not at all. First, I entered all my debt agreements with sound mind. No one has dictated what I do with my money besides me. If you can't say the same, then you should hire a lawyer and go to court immediately.
So did I but I can't say I liked it.
Second, debt doesn't necessarily cost money to use. For instance, my consumer credit card is paid in full monthly and *makes* me money through bonuses simply by leveraging revolving monthly debt. Why would I ever get rid of that for the sole benefit of saying that "Im debt free"?