I know this is a slower process than you might like but $3.3M in debt is a lot for most people.

You’ll still be personally responsible for the debt and it will still show up on your credit report/DTI if that’s what you’re trying to pull off.You’ll increase your interest rate by 2-5%?

AppFolio is great for property managers, but investors often use Stessa, REI Hub, or Buildium for tracking income, expenses, and tax reporting.

Are there any tax advantages or disadvantages to my being both a resident and a landlord?  

More like a 101 of taxation: you had a reserve of losses -> it helps when you have profits.And a tax geek addendum:I also do not see a direct link to cost segregation benefits here.

Of course, I had to make additional assumptions about the cost of property taxes, insurance etc. 

Not looking forward to losses, just meant in the sense that I have a new STR and will expect to incur losses in year 1 and this is advantageous from a tax perspective in a sense.

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.

A high property tax rate will increase the taxes more quickly as a percentage of total expenses when the property value increases.

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).