@Kenzer Hodgson For your STR, an umbrella policy can provide liability coverage, but an LLC offers additional asset protection by separating your personal and business assets, which can be valuable in case of lawsuits or audits.

Like most, I was evicting tenants that I incurred through property purchases.

Incurring losses every year will mean that the losses will be suspended and carried forward and will offset future passive income.

This could allow you to use the full amount for purchasing real estate without needing to sell your stocks outright and incurring significant tax implications.

There is some additional information that wasn't mentioned in your post above which sheds a different light on the situation.  1.

Duplex have different zoning that may permit additional units.

.* Additional Charges: Jenny requested that I deposit on her checking account an additional $20-25k for her to purchase furniture, which I refused because I thought it was very strange, opting to give my card # instead.* Work Quality: Jenny never showed up to the house, she sent 2 people instead, she never mentioned she would not show up herself, she never asked for approval to send two others instead, they did not complete the job, and there were multiple unauthorized charges on my card.* Receipts and Expenses: Once I brought to Jenny's attention that we were 20k above budget, she refused for days to give me the receipts, saying that I needed to give her my credit card statement first.

Simultaneous to that, negotiate price reductions to the greatest extent possible because of this extra cost you are incurring. 

If your project incurs losses, they can help determine if those losses offset your other income or if they are carried forward.

Additionally, when a problem arises, those problems get addressed and all parties involved are updated.Being a property manager is a hands-on / high touch vertical.