This outlook is reflected in the prices resulting in poor initial cash flow but historically great long term cash flow. 

Like @Collin Hays said, it is being driven more by neighbors tired of poor STR owners not keeping things sorted.We only look for places in vacation areas with a long history of owner driven STRs vs big cities and the like.

Concessions, when used poorly are dangerous to your business.

If they are poorly qualified, let them know now that they don't meet requirements. 

Also, I noticed his office has poor controls over sensitive data.

Yes, you bought what seems like a good deal on paper, but in reality, you own an old apartment building in a neighborhood with poor security, possibly surrounded by long-vacant shops, streets piled with garbage, and a poorly managed community.

Purchase price: $2,800,000 Cash invested: $560,000 The property is a three-story multi-family residential building with six independent units, initially facing significant challenges due to poor conditions.Renovation Investment Summary:- **Structural Repairs:** $250,000- **Kitchen Modernization:** $100,000- **Bathroom Updates:** $50,000- **Exterior Improvements:** $100,000- **Holding Costs:** $50,000- **Property Taxes:** $30,000- **Insurance Costs:** $10,000- **Management Services:** $10,000

I am confident price is your issue especially if you are deriving the price off a poor comp (smaller unit, etc) and then applying arbitrary adjustments.  

Just because a buyer doesn't fit the bank criteria, does not mean that they are a poor borrower.

One of the first books Dave gave me to read was, Rich Dad Poor Dad.