Summit Seeker's plan seems to have a major variable, that could be a fatal flaw, in the part about renting out the first condo.
First, you have to assume someone is going to want to rent something like that for even $800 a month. If you can pass that hurdle, you assume someone is going to not think of the obvious--This is going to be a forclosure in a year. Some deals are too good to be true.
For myself, I avoid like the plague, condos to rent that even have a hint of that sceanario. Counting on the naive to rent something like that is not a winning strategy right now. There are a lot of decent choices out there, and rents seem to be dropping for much better places than a crackerbox condo in Belltown.
Sometimes one has to take responsiblity and the resultant bath for their own mistakes and greed. Just another factor to consider. I would stop advising that friend about what to do, because if it works out badly, you wll be blamed.