IT will only complicate your access to cash and leverage without having any positive benefits.

If this is answered elsewhere or if anyone knows of a blog post or video that addresses this, please share.I might be overthinking or over-complicating this,.Thank you,

People elect to be taxed as S Corp to save on self employment taxes, but rental income are inherently not subject to SE tax, thus S election is not needed.S Corp also complicates the transaction if you ever want to sale. 

In some states, such as Virginia, that would complicate any collections efforts, depending on the terms of the previous lease and whether the proper assignments of interest were executed.

It's not really that complicated to buy out of state.

Our (very seasoned) real estate attorney said that he had just closed a $12million dollar deal that wasn’t NEARLY as complicated as this one, and he brought one of his new junior associates to the closing as a learning opportunity.

The calculator was WAY less complicated than I thought it was going to be so that was a relief.  

I think you are over complicating it. 

This change alone stands to gain me ~$150k+ in equity due to the increase in NOI.My concern is that firing this PM may prove complicated due to his status as a tenant.

@Christopher BerggrenYou appear to be complicating  your analysis.