Honestly seems like a little overkill on this decision - unless its strictly a rate-term refinance because rates have dropped, it usually just should come down to a side by side comparison of status quo vs. refinanced (+ how any cash-out capital is deployed)

This leads you to a decision, whether you are aiming to be a passive investor or an active investor.

Can anyone give me some advice, steps I may be missing to make a confident decision on making my first deal? 

An STR that is poorly managed may leave the PM without his or her portion of the income, but it may set up the owner to lose the property if that cash flow was needed to pay the mortgage.

Especially in blue states, if you’ve gone through an eviction that generally takes multi months, it’s a clear indication of poor behavior in most instances.

After that, make the decision based on what matters for you the most.I've tested RentRedi myself.

The best decisions come when you get diverse input and see things from different angles.Thanks for sharing this post.

. - Many of the Renter's Insurance policies do offer limited damage protection to owner, so it may be a good business decision for an owner to pay while tenant being evicted.Property managers CANNOT get liability insurance on a property they have no ownership interest in.

There will always be inefficiencies in the real estate sales cycle because of that human inefficiency in making decisions.

Taking financial advice from people who have made a life of consistent bad financial decisions is never a good idea.