Even if the rental has a decent cash flow with additional flood insurance, we're still not sure we want to take on that risk as we are out-of-state investors (planning to move back to KY in the future, but not now) and we don't like that it will potentially bring down the perceived value when we try to sell it in the future.The seller has never lived there and has not provided any information on if it has flooded before or not. 

Today poor means negative cash flow.  

IMO it’s hard for me to sell a great cash flowing asset.

That is a big difference in the amount of wear and tear on a property.

There are a lot of hotels right now that are failing and going under due to low cash flow -so its a failing hotel.

With the upswing in the country's short-term and mid-term rental markets, a unique opportunity is presenting itself to house hackers during a time when it's harder to cash flow than it was a few years ago.

Cleveland and Dayton can be great markets for high cash flow and low purchase prices, but you need to be careful when navigating the neighborhoods so you're not buying in a D/F class area where no property managers will manage and where you'll never see any positive cash flow.

If the bonus depreciation amounts go up in the future again, can we capture the other 60% if we still meet the threshold?

It may be tempting to treat them as one property and do what is called "cross collateralization" in order to maximize the amount you can borrow.

If everyone took the cash for keys approach, then the odds of a LL getting such a tenant increases.I have never had to do a cash for keys.