That being said, there are still good deals out there depending on your level of experience and risk tolerance.

We renovated upper unit and currently live in lower unit.

One thing they have that helps them is typically the interest rate charged which is typically lower than other Lenders but I have never heard or have seen any person ***** about the interest rate they were charged and it was responsible for and why they failed. 

I have an opportunity to purchase this property, and tear it down to construct a 4 or 5 level condo type building (which is what is being done by the local developers in this area).

This created opportunities for investors.Institutional money prefers lower risk investments which were traditionally A Rated Bonds.

Luckily in the lower priced house ranges around Chicagoland the rents don't really go down. 

Often you can get a refi sooner than that but it will be based off of the lower of the appraised value or the purchase price. 

This is in what I’d call about an an A- or B+ neighborhood, in lower income neighborhoods perhaps people wait longer I am not sure. 

Also, it can take a while before you get the short-term rental up to a reasonable occupancy level and nightly rate.

That’s why I go no lower than 8.34% (One month rent) for Vacancy reserves.  5% for CapEx may be too low.