What structure would be recommended for holding personal assets and investment properties, including rentals, to optimize anonymity, asset protection, and tax benefits?

I promise you will have options once you finish renovating.If you purchased correctly (location & purchase price), you will have enough equity so that you can either sell it for tax free capital gains, cash out refinance (if mortgage rates are lower), or pull a HELOC to acquire your next property!

This creates two loan payments ($100,000 of equity and $300,000 on the new mortgage).Key NumbersHome Equity Loan Interest Rate: 6%Mortgage Interest Rate: 7%Rental Income: $3,000 per monthExpenses (management, taxes, insurance, maintenance): $800 per monthIncome and ExpensesMonthly Rental Income: $3,000Monthly Expenses: $800Monthly Mortgage Payment: $2,000ExplanationThe investor earns $3,000 in rent each month.They pay $2,000 on the investment property mortgage and $800 on other expenses.This leaves $200 profit each month or $2,400 per year.However, you have to pay $6,000 interest on the equity borrowed.This leaves you with an annual loss of $3,600.While the rental property generates positive monthly income, the interest cost of borrowing the initial $100,000 results in an overall loss.

Grow wide first, then deep (pay off)- your little expenses add up fast

Outside systems like plumbing, sewage, and the water heater should be in good condition, and make sure there are no signs of pests.Additionally, look into property taxes, insurance costs, and zoning laws that could affect future development.

It's just that I see how far off we are and, being inexperienced, am naturally inclined to think I'm being too cautious.

This would allow you to indefinitely defer all of the tax if you sold, and use the tax you would have had to pay, to purchase something nicer in an area with a greater growth potential.   

In your case, you are probably better off buying a break-even deal in Tampa then a deal with $200 cash flow OOS.

This allows you to report the rental income and expenses directly on Schedule E of your joint tax return, simplifying your tax filing process.

I personally like the BRRRR strategy - it's not easy to pull off but it's simple and it works in theory.