Wowza, quite the checklist. You may be in luck here, as we have quite a few folks who leverage real estate for FIRE goals. Afraid that's out of my league..I'm a "low cost, index-fund, spend less than you make" old guy, who's on track to FIRE in 18 months. Keep up your motivation, and beat me to the finish line! I'm sure you'll find folks here to help you on your jouney.