You can use this property to hedge any others that you add that may only cover themselves, or require supplement until they are paid off.HOWEVER, if you have decided that your goal is to use Real Estate as a stepping stone to build wealth by upgrading the property you hold each time (condo to house, house to 4-plex, 4-plex to 8 unit, etc) then I think you are right to sell now while you think the property is at the top of it's appreciation.It will be hard for anyone on BP to tell you what to do as we don't know your goal.You are right. 

These seem like more supplemental insurance policies on top of home owners insurance.

Your actual property taxes alone on that will be over $10K a year in 2025 and don't forget about that supplement tax headed your way.I would suggest keeping the others and maybe changing to LTR if that will give you consistent cash flows.  

In your experience how feasible would it be to use an accounting degree to supplement income while running another business?

From 2020 to 2023, I used a HELOC to supplement my available cash to BRRRR as many single family long term rental properties as I could as fast as I could.

.🔹 How It Works:If your rental income falls short of covering your mortgage (PITI), you can use liquid assets to supplement your income.

Loan Programs: Conventional loans (>$7.5M), small balance loans (<$7.5M), lease up / near-stabilization loans, 2ndlien supplemental loans, student housing, seniors housing, MHC, green financing, etc.2.

If It is a wholesale DSCR lender that also does TRID loans, they might require a bit more paperwork, such as a VOM, mortgage statements for properties currently owned, and credit supplements on mortgages on your credit report.

Has she even received a supplemental tax bill yet? 

How much will the increased cashflow supplement your anticipated SSI?