Everything matters, from picture quality to online presence.

Whether it's a legal demand for compliance or simply an email, it doesn't really matter; just make sure everything is in writing. 

@Andrew Steffens the pool of buyers that have six figures of cash (you really need about $150k in cash to buy a $500k STR), have some subject matter expertise, AND want to self manage is even smaller. 

Expect delays and unexpected expenses: No matter how straightforward the project seems, having a contingency fund for emergencies is essential.Your Team matters.

The fact of the matter is that real estate is a long game and expenses will come up. 

If it is accrual, then when you actually make the payment does not matter.  

You need to develop a subject matter expertise and treat this like the hands on business that it is. 

Interest rates don't matter (much)!

Making matters even worse, the properties most are buying (the lower tier properties) are disproportionately impacted by operating costs and cap ex.  

If passive income and ease of management matter more than squeezing out every last dollar of equity, a turnkey property could be a great move for you.