that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases.

In some areas certain provisions MUST be included in a lease.  

That does not include any capital expenses. 

I am getting to the point of wanting to back out due to the 27k combined Closing costs, not including down payment. seems like a I should look into finding a new loan officer.

The OP made this math easier for me, since he let us know that he is clearing $2300 a month after all his fees, so that means the only cost he isn't including in that $2300 would be his principal and interest. 

Creative ApproachesIf the organization is hesitant about a sale, consider proposing creative terms:Seller Financing: The non-profit could retain an income stream from the property by financing the purchase.Partnership or Lease-Purchase Agreement: Offer to lease the property with an option to buy, giving them time to evaluate the relationship.Donation or Support: Consider including a donation or offering support for their mission as part of the deal.

The important things to consider about HOA fees is that they usually include some utilities: Water/Sewer, Trash, sometimes shared amenities like gym, clubhouse, pool, and they are saving you the time and headache for property maintenance: lawn care, tree timing, roof, siding, etc.

Cost was about a dollar a mailer and my assistant's time, including postage.

It added new stipulation, including the ability for housing providers to get 100% back rent owed even for tenants that have moved out already.

Red flags for me include people who are overly optimistic without considering risks or those who don’t seem to have a clear plan for their contributions to the partnership.