You plan to declare the rental income on your tax returns either way, right? 

We are ready to try AIr BB/ fully furnished short term rental as we believe we can double our income on the rental property. 

So the question is not about income, the question is more about hassle, wear on the property, damage and other such things.

Once I can verify their income and past rental history, then I schedule a showing.

I’m a software engineer (frontend web dev) working remotely in Berryville VA.

In my opinion, I wouldn't worry as much about cash flow and just make sure your PITI (principal interest tax & insurance) less rental income is less than you would pay for rent in that particular area. 

So, potentially in theory if you get ahead by one "payment" you are already doing pretty good.You need to be "ahead" on your income/loss, not "behind."

I’ve had a few clients close recently on properties in Black Hawk/Gilpin County and the income numbers there are fantastic, Gilpin is also quite friendly toward STR investment properties.

You need to consider factors such as location, condition, potential rental income, necessary repairs, and your own loan terms.

Looking to buy an income property in my local area.I don't know where/how to start in other areas so open to feedback on this topic too.Any guidance would be appreciated.