Will I be able to overcome it's reputation in getting mid term renters?

If you're looking to get into STRs, you need @Avery Carl's book, Short Term Rental, Long Term Wealth, published by BP. 

So appreciate your thoughtful and detailed response. 

The location is ideal, as it’s situated in a neighborhood that permits short-term rentals (STRs), making it a great investment opportunity.

.: @Jaycee Greene flip and fix, under 150kSomething like this: https://www.realtor.com/realestateandhomes-detail/1542-Haine...?

Visit with people there and you'll get a more detailed look at things from people actively working in the areas.

Zach proceeds to get on the phone to, I suppose, “get me together”, with their details as if I didn’t just experience their unorganized process.

If you were renting to an only a couple as a long term tenant and they beat each other up (domestic violence) your liability is minimal.  

Must have tools: you need some type of evaluation metric and/or tool that you are comfortable with and are willing to walk about from a deal if it doesn't meet your requirements.also, a deal is a term for a transaction, not to be confused with a "good deal".

Purchase price: $320,000 Currently have a long term renter, the rent pays the mortgage and other expenses but provides no cash flow.