Risks include but not limited to buying a poor position ( no equity ), horrible property condition, no exit strategy, evicting occupants, getting foreclosed on by a senior MTG. 

I have been around the business of real estate my whole life (mother owns and runs a title agency) but never actually put any of my own effort into it.

want to limit the amount of tax they pay in real estate, and in life. 

Current condition: The Good - Shingles and kitchen are about 9 years old and in great shapeNeeds: Foundation needs bracing, mortor work, drain tile, (basement is not tall enough to be considered living space, any ideas?

Look at the condition of the other properties, the businesses that are tenants, try to discover rents paid, how long they have been there, etc. 

.- Duplex. 3bd + 1ba, 1bd + 1ba- Somewhat dated, could use cosmetic updates but otherwise appears to be in good condition- $129,000I've spent some time looking at rental listings in the immediate area and my rough estimates are that you could get at least $500/mo for the 1bd and $1000/mo for the 3bd for a total of $1500/mo before any updates or renovations.

Okay, so now that my subject line has caught your attention...I'm trying to work out a proof of concept on real estate transactions that may be affected by the seller's end of life planning.

I explained at that time that i understood if they needed to go that route, but I explained that I couldn't maintain the rent that far below market.Fast forward to now and as more time goes on, they are growing on me as neighbors and so not only would i not want the wrath of the neighborhood if they are forced to move, i also would like to keep tenants that i know are great neighbors while i reside there.So all that being said, if you were in my shoes would you take an income hit and not increase the rent or only increase it by $75 or so in favor of maintaining a quality life with good neighbors?

Although i have reasonable amount of cash to get this business off the ground, i just struggled to get the numbers to work (ie sufficient cash flow from buy and holds to support my life without a W2 job). 

REI is no different than anything else that piques your interest in life...you spend time learning and doing it to see if you like it.