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.

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.

But ya have to make some educated prognostications in life.Add this to the information your processing - What your talking about doing is eliminating around $4000 or interest expense (which is deductible anyway so really could be a real impact of eliminating $2800 or so) of debt in exchange for paying over $10K in capital gains tax (don't forget possible state gains tax as well).  

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.   

Did you inherit this home with a step up in tax basis or will you need to pay taxes on any gains if you sell?

Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

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

Often the best risk, hassle and tax-free approach is to pay down debt.If you have a car note, credit cards, etc pay those off first.