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. 

Understand cash flow lower then say 500 bucks a month is a myth anyway.

So, there's more than one way to create more cash flow than refinancing:-). 

Hello Zachary,  You are correct in looking at the Mid-West for cash flow. 

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.

In Columbus, appreciation is between 7-17%, and cash flow is at 8-12%. 

I know that my current cash flow is a result of the unit being my primary residence first, and that not all units will cash flow like this, but can't help the feeling that I should be expanding my rental portfolio over the years.

(No mortgage on any).the cash flow is a total of $3,100 a monthDo portfolio loans exist for these kind of situations?

When does the cash flow start? 

Over time your Tampa investment will start to cash flow.