I think from an investment perspective saying it is cash flow positive because it was bought before the run up is a flawed way at looking at it. I think you need to look at it from if you sold this property could the capital produce more money in an investment elsewhere. Of course anything pre boom will be way cash positive but that doesn't mean its a good investment.
As far as Condo risk goes i agree with the above that if the reserve fund study has reasonable values for things like re-siding / re-furbishing exterior, boilers, Elevators, Windows and Doors if they are included in the boards responsibility. If those big things have realistic values then you should be okay.
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