Dilemma: duplex comps in the area are scarce and mediocre.

Just curious, not challenging your statement but how does bankruptcy "demonstrates financial immaturity and risk" since: Bankruptcies resulting from unpaid medical bills will affect nearly 2 million people this year—making health care the No. 1 cause of such filings, and outpacing bankruptcies due to credit-card bills or unpaid mortgages, according to new data.

I was a Realtor for a short while but needed to get a steady income and health benefits back when my wife and I both started realizing our health issues were very unstable.

Did the person last reside with a relative, in jail, in a mental health facility, in a shelter, a recently foreclosed meth house?  

I cannot say I have completely understood your questions or dilemma.

After turning 30 and having our first daughter, I flipped my mental state 180° and began obsessing over my health and future.I've been scouring these forums and listening to the Bigger Pockets podcast.

Health is ALWAYS a must, ensure you keep it as long as you can.  

After finding out about the smoking, inviting others over to live, dogs pooping on hallway carpets (carpets to be replaced) and used up last months rent from previous owner, sellers agent now tells me (after the fact and sale) that this tenant reported previous owner to board of health because thats how she settles things.  

Having everything together in one place will help you see the overall health of your business plus these are related to each other, for example, your mortgage payment consists of interest (P&L item) and principal (liability) so you don't want to track the interest only on one software and the principal on another.

My wife and I are exploring options for financing our first rental properties.  We would like to free up some cash to make improvements on our current home, move out into a multi-family property, rent the other units ...