@Julian Hickman - I found this website where you can see the number of positions posted in your area to gauge demand for MTR for medical professionals.

Water Pressure Gauge: Water pressure levels should be in between 40psi-80psi and can be checked at your water heater or hose bib if it is regulated.

A big concern is the pressure to find deals right now.

I would try to keep it as a 3 bedroom and gauge the market interest for the 3 bedrooms.

While I like the "roommate" idea (and one or two others) you are feeling some pressure and, between that and a lack of experience vetting tenants, you have an increased possibility of being too hasty and allowing the "wrong" tenant in. 

Many municipalities are under pressure from the hotel industry to ban AirBnB's and some HOA's don't like them.

My cashflow is roughly about 32-35K per year for the properties and his about 29-32K as I have one more property (hard to gauge b/c of the turnovers and issues).   

Hey Real Estate People! I’m soliciting input and feedback -Most of us love the idea of outsourcing lead-generation and cold calling…Despite this, does anybody find it challenging to acquire qualified and high-caliber ...

At least that would have worked until recently.. but now the negative pressure in the form of very high interest rates is going to slow appreciation.  

If the insulation is wet, it should be replaced so the substrate does not deteriorate from the moisture, compounding the problem.Once you've determined what is causing the ponding and address it; your next step would be to pressure wash the roof area to remove any coating no longer adhered to the roof system.