However, I was talking to a DSCR loan officer about a property I was looking at and they told me that they would only lend to an entity like a LLC or corporation; they would not lend to me individually.

They have offices in many states and handle thousands of rentals.

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?)

Someone here can probably speak more intelligently on the process too. 

., business travel, home office), optimizing mixed-income structures✔ Long-term tax planning: Strategies to reduce tax liabilities and avoid unexpected tax payments✔ Proactive advisory & clear communication: Ability to explain complex tax matters in simple terms and provide proactive tax-saving solutionsAdditional Considerations:Expertise in tax treatment of travel to Germany (e.g., for real estate management)Experience with compliance in both countriesIf you meet these qualifications and are interested in working together, or know someone who meets our requests, please send a message. 

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

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. 

Find a decently priced loan officer or two and stick with them.

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.