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

I think the biggest tip-off is when a new name appears on the HO's policy. 

However, the biggest maintenance expense, by far, is lawn care and snow removal.  

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.

Because, even if you have the biggest grand slam, sure thing deal in the world, you don't have any trust from investors.  

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

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.

3) What undervalued neighborhood(s)/street(s) do you forsee as having the biggest appreciation opportunities?

It actually offsets my other income...I can grow it entirely tax free....Downsides of course are management, management, management.

Biggest mistake of my life was not holding 50 or so more of the 500 I flipped, HUGE mistake