This is one of the biggest gentrification areas in Indianapolis and will be a great long-term hold.The market value is $550,000.

My biggest concern is: I would like to have this property cash flow $200 monthly and I'm not sure if the market would be able to support that high amount of rent.

There should also be records with the city of the guest house being built (if not, easy enough to report it to the city) and copies of his tax returns.

You'll need city approval even though it sounds like the zoning is favorable.

I know the city inside and out, best places to invest, pitfalls, etc.

Most city/county regulations want no less than 1 million in liability, so we require that for any clients.

To answer your question directly, the biggest risk, and one that 99% of new wholesalers suffer from, is wasting your time learning the intricacies of wholesaling when it really doesn't matter.

The secret, and the biggest obstacle to success, is understanding that ALL, not just some. of the above list must be met. 

There is government data online to see where good schools are, low crime rates, and desirable city amenities.  

I see you’re in Phoenix, this lot is in the Silverbelle Estates subdivision south of Arizona City.