Psychology of making an offer to distress homeowner - Need Help

[Herlando Y.]

In my last post I have a house that I found while driving. I talked to the homeowner and it seems like he is running out of money to repair his distressed home. Here is what I know:

Asking Price: 290,000 - 300,000
ARV: 264,000
Repair: 70,000 - 100,000
Cashflow after reno: $1000 monthly

• We got this distressed homeowner who evicted two tenants two years ago. Those tenants did not pay rent for the past 1.5 years leaving over 18,000 in rent owed. 
• A developer approached him last year offering him $325,000 contingent on the developer getting the other properties as well. The house sat vacant for 9 months and he never heard back from him. 
• He talked to cash buyer and rejected the offer for $210,000. 
• He have 125k Equity and a 160k mortgage left on this property.
• He states he is running out of money to repair the property
• The property is need of major rehab. I got contractors going there tomorrow.
• He can not refinance the property under these conditions
• He lives 5 minutes away and have attachment issues with the property 
• ARV is very hard to determine because no house sold on his block and it is a very unique house. My loan officer pulled up the info quickly and determine it to be 240,000 to 325,000 k value. He had an appraisal that is around 260k-270k for his refinance.

My plans:

• Give him an offer over 210,000 if possible. Need to give him offer soon since I found a bank that will finance the rehab cost. I just need my contractors to give me a price and add 20% to the cost of repair.
• Turning this duplex into a triplex. It has 3700 sqft, but limited to street parking.
• Total Estimated Cost:
  • Purchase Price: 220,000
  • Closing Cost: 12,000
  • Repair: 70,000
  • Total Cost 302,000
  • Cash Flow @ Triplex = 1000 Cash flow monthly after accrued expenses, mortgage, tax, and insurance

Understanding his psychology, how do I make an offer to the homeowner that make sense for me?