Very thick, sturdy "pads" I can put down on the roof, which would be strong enough to endure any small parties my tenants might throw on this roof-deck area.  

Or if you're rather saying "good luck with that..." then you seriously underestimate me, and my level of 'resolve' after what I've endured, sir. ;-)

At least I would have a horrible experience under my belt that I had the courage to endure, rather than staying in a nice, air-conditioned conference room yet again refusing to make a decision.I'm being a little facetious. 

I would also like to point out that this can be a golden opportunity for someone who wants to mold an individual without enduring all the costs associated with training.I'm currently finishing my degree in Finance, I have 3 years of telecom sales experience, and eager to get into the mortgage profession.

That being said it's important to extrapolate the costs you will eventually have to endure down the line and see whether $550 per month per unit is enough to handle these.In my experience, it is not.

Even if you didn't lose the property like @Jimmy Moncrief's neighbor in the 70's, how many years of negative cash-flow did an owner have to endure during the down cycle?  

I expect somewhere above 70% for everything I have endured in 10 years with the Corps and all of that money is going into capital for REI.

The option fee is the fee you pay for the right to break your otherwise contractual obligation you endured to buy the property.

Anyone have any ideas of the likely loss i would have to endure?

Paint is normal wear and tear item.. and over this period of time the cost you would have had to endure with others moving in and out..