The pandemic forced people to work from home and having spaces that worked as offices became important. 

-Will it be robust enough to track additional business expenses that are NOT tied to a single property (IE; Business insurance, Home office, ETC?)

We live in Kihei now since the Lahaina fire destroyed our home, office and an investment condo.

Financing might be a challenge.I would recommend consulting with a attorney, loan officer, and CPA to discuss your specific situation and determine the best course of action. 

The renovation aimed to modernize the property, enhance its appeal to potential tenants, and maximize its long-term value.

Then, just three weeks before closing, my largest commercial tenant—who brought in as much monthly revenue as all 25 mobile home tenants combined—announced they were moving to a location closer to their main office.

We live, office, and Property Manage in Queen Creek and love it!

Hey @Raven Ye Mahar, so you should call the city and make sure but if you are renting it long term, you shouldn't be on the hook for any of the occupancy taxes.Nashville has a STR Occupancy Tax - https://www.nashville.gov/departments/finance/office-treasur...In the end, I would just call the city and get the deets that way. 

The withholding can also be stopped altogether, and only actual taxes owed will be collected by filing form MW506NRS at least 21 days prior to settlement and filing it with the Comptroller of Marylands office to get the exact actual tax owed calculated. 

The challenge with S8 in this scenario is you always have a piano over your head and all a tenant has to do is call the code office to create an issue for you.