@Anthony Saheed I would advise you to be very careful to recommend people to speculate in volatile real estate markets.

I'm being required to pay another application fee and then $600 application fee to hopefully get this approved by the Board to allow me to continue running the STR that they approved 6+ months ago. 

A lot of the popular areas in Charleston proper that are not licensed under the old laws now require the owner to live on the premises to obtain an STR license.

Both these properties have mortgages and they both are required to have insurance on them.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

A car forum that I'm a part of, and I know the owner of the forum, told me that the dedicated app required constant work and updates as phones and operating systems changed. 

For newbies, I recommend starting with a turnkey cash flow rental.

My focus is on providing either turnkey-style space for those interested in temporary, infrequent use or long-term leasing for business folks who require conference room space (or perhaps event space).

Immediately the recommendation changed and now my inspector leaves no stone unturned.

High-end properties might require a white-glove approach with customized services, while more modest properties may prioritize affordability and efficient communication.