I assume in the worst cases, even if the HOA forecloses, they would still take the property subject to the first (me)  Is that correct or is there something lurking out there that I am not aware of?

A flat roof can be just as durable as a normal roof sloped if it is installed correctly and I don't see how it can be more of a fire hazard since it is wood like the rest of the roof.  

Just to be clear, you currently have a mortgage on your investment property (i.e. not on your personal home) and you are planning on taking out a HELOC on that same property with a higher loan balance, but at a lower interest rate - is that correct? 

These decisions take time and add a ton of value if done correctly, so if you were doing that, your adding value.

If you can estimate your numbers correctly, and you can find properties, you can't even supply for all the investors that you will find.

We spent roughly 20k in the conversion (conforming windows are expensive) as well as correcting some drainage and sewer issues.

Property management is a business and if not done correctly you will fail.

On the flip side there is a need for regular family rental homes, that may not need quite as much work in between tenants, or if you are smart and update the property correctly you, there will never be much need to fix up in between tenants, after installing hardwood floors, tile, waterproof vinyl Allure, granite counters, tile surround showers, etc.  

@Scott McIlvaineWelcome to BP Scott, you are correct that the numbers are a little iffy around our area, but I have seen local investors do quite well in markets many would consider expensive like Newtown, Doylestown & New Hope.

They turned out to be rather incompetent, making mistakes, correcting them, un-correcting them, correcting them again and finally cancelling my policy due to the house not meeting their criteria which has never changed.So for the last couple days I have been shopping around.