I work in analytics consulting and have managed my finances and investments well by myself. 401k, investment accounts, high yield savings account, own a house in a nice neighborhood with a traditional 30-yr mortgage, etc. 

I'm looking to get some insight on reasons why this deal isn't moving if the numbers makes sense, however it's in a really challenging Southside neighborhood in Chicago.

Am I alone in finding that in today's market, wholesalers tend to be able to bring properties at the same price points as you can find by shopping at foreclosure auctions?

It's not in a neighborhood that I would invest in for a rental and the market doesn't look that great for a flip. 

We see duplexes going for 1900/mo in the neighborhood and newer apartments in the 3000/mo range. 

A SFH in a good location beats a duplex in a rough or questionable neighborhood.

Being so, there are some very nice areas, as well as some C/D class neighborhoods. 

It’s worth continuing to shop around or even speaking with a mortgage broker who can connect you with a lender who might be more flexible with these terms.Also, keep in mind that every lender has different guidelines, so it may take a bit of persistence to find one that aligns with your needs.

I prefer to avoid D/F neighborhoods.

I've had very similar types of projects that took vastly different effort due to neighborhood opposition, or unforeseen City requests.