There are properties in Avondale, Hermosa, Irving Park, Jefferson Park that you can purchase for $500-600k and see positive cash flow of about $200/unit. 

Seems real hard to find a deal producing positive cash flow with 0 down but then again I just started with this.

I've looked at the market here in Orem Utah which is where I want to be because it's close to Utah Valley University where the renting rules are more lenient than for BYU Students, and just from looking at the mortgages that I calculate, it would be very tough to find a rental property that I could live in and cash flow positively. 

It’s a great market and in the distant future it will be a market I would like to look for opportunities in for population growth, job growth, infrastructure, positioning for climate change (very long term) etc..

No tenant, no matter how good could leave the place without some disrepair in 6 years.Tl;dr 40k house on market 200 days, wondering why an investor hasn't picked it up if the simple act of getting it is already positive cash flow. 

the  rental income for  present and  future rental income  can be  counted to a certain degree  ...so this should make your  dti ratio lower ......in most cases  rental properties will   cash flow  positively  or at least  break even   from a lenders  qualifying perspective  ...fyi - lenders  will use  your schedule E  for analyzing rental income  for properties  owned for  more than 1 year

What does he do for a living, a position of power or negotiator?

For mobility issues, generally showers are preferred, no lifting of the feet to step over a tub side or to pull oneself out of the low sitting position. 

I am second-position mortgage holder on a commercial (non-residential in any way) property in Allegheny County, Pennsylvania. 

You are actually in the perfect position to start implementing the Nomad model (what I’m used to calling the version of house hacking that I do).The reason you’re in a good position is because you already have one house, and you bought it a year ago.In Nomad, you buy another house for your family, move in, and convert current house to a rental.