Based off your first house hack, would you say that the deal you took was worth it in the end, maybe based off the experience or could you have found better? 

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Based on an appraised value of $255k and rent of $1,600, you're running VERY tight on a 1.0 DSCR at these interest rates.

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I would like to address the concerns that you brought up and hopefully help clarify any confussion and see if you are still in the industry looking for financing options. 

Check in with @Joseph Chiofalo for STR loan options.

What kind of risk are you creating based on the nature of your real estate activities?

The most expensive cost for me was the holding time and the stress of possibly raising the house by a foot from the Base Flood Elevation.   

The deal was valued based on a recent sale of the local Holiday Inn, (only real competition for us) which also needed to undergo renovation.

It sounds like a DSCR cash out refinance would good option for you as you can be in an LLC, no DTIs, and there are no concentration limits when it comes to how many you can do.