It's been very handshake agreement, and he's a friend so no issues. 

This gives you a chance to get eyes on the property regularly, ensure dirt and debris are not building up and you catch issues while they're small.

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. 

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?

It won’t technically be an ADU as I can permit a full second dwelling, but it will be similar to a large guest house. 

For tech issues, it depends on what it is.

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.