The lighter the color, the more the "flaws" stand out.

The appraisal concept is flawed I think because it's hard to account for value growth if you're only looking at past values.

When I initially walked the property I noticed that there were 4 designated covered parking spots for tenants in my property and 4 additional uncovered parking spaces.

What do we need to do to ensure we are not liable for damage that a buyer might uncover later, that we are currently not aware of?

Since this is our first project like this, I'd love opinions from those with more experience...do you see fatal flaws with the strategy, are we missing the boat on anything huge, etc. 

It can definitely be a Big flaw. 

Local is always a great place to start with the assumption you know the market, the challenges, advantages which can make it easier to uncover the best deal. 

All in the chance that you can uncover a deal to make some money.

Your "friend" is a scammer and that is a character flaw that does not change.

Several thousand dollars in uncovered repairs is a cost of doing business that isn't going to have much of an affect in the long run (especially if you're saving it in lower premium for the higher deductible); whereas several HUNDRED thousand dollars in uncovered liability judgement is going to hurt, really bad.2) Once you grow to a certain level, you become more of a target for lawsuits.