I think my post is a bit all over the place just to cover the main events that tie together.  

Distributions from an LLC are not a taxable event.

In the event that the activity is determined to be dealing inventory by the IRS, the total taxes on the profit are high...

Understanding the impact of operation expenses and cap ex when those events occurs is really critical to the performance of real estate. 

Scott Scheel and Ray Alcorn are also very solid - I speak at their events regularly.  

This step ensures compliance with local regulations.From my experience, when I had an STR in Cleveland, I only did the regular rental registration, so make sure you complete both registrations to avoid any issues.Cleveland is a popular spot for STRs, especially for visitors coming for sporting events and medical purposes.

Any suggestions on where to start, what to look for, recommended reading or social events.

In fact, even if the property were to appreciate to the point where a favorable refinance event existed for @Eli Jerman I would most likely still advise against re-titling the property in an LLC.

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When did you enter, what type of property, what is the goal, where would you place the gains, what are taxable events associated with the exit, and more.