Thank you for your service and well done thinking ahead of living off financially free. 

Many nuances are ahead of us such as a potential LLC, real estate professional status, cost segregation, etc.

Also, I would run the #s ahead of time (treat it as if you will move out in a year or 2) and see if it cash flows once you buy the next one (and depending where it is... it could potentially be a long-term, short-term, mid-term... pay attention to HOA rules if they exist when determining asset class). 

To me it seems that you are ahead of the game, what would you increase it by if you did?

Really just more curious than anything, as to how many bookings are last minute (week of) vs a month+ ahead of time?

All I use it for is to inspect roofs and check the number of vehicles parked outside my competition. 

What this means is that if you get into an accident in your vehicle. 

One neighbor has had three new vehicles in the time I have driven this old beater.

Roth IRA is tax-deferred vehicle.

Real estate serves as a good investment vehicle despite the seemingly waste of money. 7 years we owned the home and only stayed in it 2 months a year and it still appreciated more than we spent on it.