What are your thoughts on doing  A to B and B to C transaction?

Curious to hear responses on this, as it is a question I am debating too, before beginning to invest in the Columbus area.A nice rule of thumb I heard is that worse areas tend to have better cash flow potential but lower appreciation potential. 

On a similar note, lower-income people aren't necessarily that bad to deal with.

You can not expect to successfully operate your business without knowing the rules.Keep in mind lower end rentals will be labour intensive to manage.

As it relates to flipping, how do I protect myself from a buyer who may want to cut me out of the deal so that he/she can take over the property for a lower price?  

@Matt Boyle days on market are typically less in IN just cause the market is a little smaller and as far as rentals go it shows a higher profit cause of taxes being lower. 

Is it too late to bring up that I will be working with an agent on my side of the transaction?

As I have less than a month at this point to refinance and not pay the extension, should I keep looking for private money or lenders with high upfront points and chase the higher 75%-80% LTV, or pay the extension fees and cash out at 70% LTV with fewer fees and lower interest rates? 

You could lower rent to fill a vacancy only to discover it is someone that suddenly can't pay rent (lower quality tenant).  

Just like what Johnson said, the house split into two 1/1 units, upper and lower.