By doing these two things my hope is that I will further expand my business as well as meet like minded individuals who equally have a drive to create and/or find  smart advantageous opportunities.

I plan to give fair and equal treatment to both units in terms of rent raises.

In other words, have your entity ownership worked out BEFORE you put a property into it or it may become more costly later on....Pittsburgh has transfer taxes higher than 2%, and splitting it equally is customary but not mandatory (HUD and Fannie require the buyer to pay the transfer tax in full since they are exempt from transfer tax payments).

Everything else being equal, I'd like to be in an area where I'm in the top half, or even the top quarter on that scale. 

Napoleon Hill (Think and Grow Rich) said every adversity, every failure, every heartache carries with it the seed of an equal or greater benefit.

If I read your response correctly, in your scenario #1 and #2,  You would be paying for the full cost of the repairs anyway by receiving less rent equaling the repairs or paying the tenant for their hired contractor (instead of yours). #3 seems like the repairs would not get done at all, which means there will most likely be a low appraisal in the future spoiling their financing at the end. 

Consider the 2 1/2% rule...Take your purchase price as the base number.Use a service (like rent-o-meter) to see what typical rents are in the surrounding area and look for a comparable property.If monthly rent doesn't at least equal 2 1/2% of the purchase price... walk away. 

Assuming all else equal with the labor participation rate, large infrastructure spending will tighten the labor market even more.

So, if you have a property with a $100,000 seller financed mortgage and the contract of sale is for $200,000 – normally the mortgage would have to be paid off – unless you substitute it for another property with equal or greater value and equity – so you don’t pay off the mortgage and walk with $200,000 instead of $100,000.

I think $800 is reasonable for a 2 bedroom in the area - all other things being equal.