Being that STR revenues are on a decline & the market is a bit saturated, it's a scary prospect.

I would decline this application.

Higher-income residents then leave the area, perpetuating a cycle of declining city income, services, and increased crime.

You are just going to be losing money for a long time with little to no upside in the near future if you consider real estate is likely going to decline in value in the near future after just running up? 

The cash flow is decent but you have the usual declining neighbourhood challenges like poor snow removal, crime, zombie properties, less responsible tenants, etc.

@Victoria Ho Sauk Village could be profitable, but it is right by the border so you will continue to see decline as people shift across.

I declined, pointing out that unless he intends to change the front door lock on me to lock me out, it wouldn't do anything.

Ok, so let me get this straight.You knew there was a basement, you knew that older homes had drainage problems, you had the choice of buying a rider for $100 which you declined, the basement floods and causes $4k of damage............and it's the fault of the house because it's a "pig"?

We just had one declined because, although the customer qualified, their system didn't recognize the physical address. 

And even though the pop has been slightly declining, many millennials have been moving to Cleveland, which I see as a good sign.