@Kate Weinberg (and others who expressed interest in this topic).This is almost identical to a situation I found myself in a couple years ago and we periodically hear from others struggling to find a good home for their capital.BTW, average returns for Large Multi-family is 8-12% Cash on Cash or 15-20% IRR for a 3-5yr hold.I am in the midst of writing a blog post about the various options I considered (stocks, private lending, SFH portfolio, Multi Family Portfolio, private equity, REITs, etc) and my logic behind selecting what i did.If it would be helpful, I can share a draft of the upcoming post with you soon.

All homes on the exact sized lot as mine have an identical lot valuation.

Your experience sounds practically identical to mine.  

Claiming you need to hide your identity and location is suspicious. 

Identical duplex on the same street (just few blocks down the road from mine) went pending nearly $70,000 higher than what I'm paying.

Recent capex: Both HVAC 5 years old, water heaters 4 years oldUnit one: 964 sq ft, vacant, market rent $1500 (I saw an identical house down the street with a "for rent" sign at $1575)Unit two: 964 sq ft, rented, $1250Property taxes: $5,500 / yrThe seller seems antsy to sell (the owner is a realtor and apparently emailed our realtor twice yesterday asking if we're interested), so I'm targeting $400K, with 20% down.The current owner provided these numbers:Annual operating expenses: $6,000Annual utilities: $4,000Annual insurance: $600When I use DealCheck, sometimes it has positive cashflow and sometimes it doesn't, depending on what I put for vacancy, capex, maintenance, etc.

Cozy is the preferred method of rent collection, but this tenant refuses to set it up due to a fear of a past identity theft issue. 

There are 3, nearly identical, properties in the neighborhood that have rented units in the past year giving us an OK amount of rental data to run our analysis.

I have closed on two additional 6-unit buildings since then and gave him the business since he bailed me out.The six-unit buildings are in a pod and identical, but the premiums have gone up on each policy by more than 10%. 

Personally I find having identical decor in both baths confusing.