But those in the field still spend 2080+ hours a year doing it, plus 20-40 hours of continuing education a year, and still regularly come across issues they need to research or toss around with experienced colleagues. 

One electrician, who had been part of a previous inspection, got back to me and provided an estimate for fixing electrical issues, including addressing the knob and tube wiring. 

Hi @Matthew Masoud, I think you touched on the biggest issue with mid-term rentals.

3) If in the event zoning is an issue, or it makes more financial sense to not convert to a commercial loan, is there a way to SPLIT the quadplex so that each duplex sits in its own lot and I become the owner of two separate lots, each with one flat roof duplex?

For tech issues, it depends on what it is.

Anything with a Raleigh or Durham address doesn't work as an investment property unless a chunk of equity is left in the deal (for those needing cash flow). 

Using Philadelphia as an example, in other areas, especially the more suburban neighborhoods, you could run into ERSA, steep slope, and more common to encounter interpretation issues on the part of the plans examiner.

The issue is it will be short term so what are you gonna do to pay it off.

:) To follow up on our conversation, each DSCR will have different requirements however I am not seeing an issue with you not having personal rental history so you should be good there.

Most investors I come across switch funding sources because of qualifying issues related to DTI.