Like 95 dollars a night cheap. 

It all depends on your risk tolerance and what helps you sleep at night.

I am crazy rolling in bed every night trying to find a way out.

Because we don't try (too hard) to look or come over as credible.What happens when you try too hard to make your girlfriend believe you were home alone last night?

Anything rented for less than 180 days is STR, whether it's for 1 night or 30 or 179.Let your broker know what you're doing; get the right coverage. 

I know there are some guys here who stay up nights figuring out how to pass generational wealth to their children successfully, looking at you, @Steve Vaughan.What are the rest of you doing?

I did a random search for a week on airbnb and the low end was $60 a night and the high end was $110.  

This can reduce occupancy and reduce the average nightly rate (as compared to a higher nightly rate and lower cleaning fee). 

Now, onto the million-dollar question: How does one embark on a real estate journey with pockets as empty as my social calendar on a Saturday night?

There's no panic, no animosity towards the tenant, no sleepless nights or hard liquor.