I have sold a couple of businesses as well, and speaking from experience, you are never more vulnerable to make a mistake than when you are sitting on a giant pile of cash.Also, I agree with @Corey Conklin - I'm a big fan of "overflow cities/towns" in the sun belt.

I have been reading and listening to real estate investing books everyday for a while now and it is something i want to pursue. 

From my experience, Aircover has been covering loss of income if there were bookings for those days. 

How many struggle in there bookings, to find way around, ask "what is this corn-dog like thing"..... 

Inside of drawers, ceiling fans, vents, cobwebs on the porch, etc.. 

Thanks to everything I’ve learned from the podcasts, books, and this community, my wife and I currently own:A triplex in MaineA single-family rental in San AntonioA single-family primary residence in Las Cruces, NM, which will become a rental when we move in a few monthsFor context, I'm an active-duty Army officer with about 12 years left until retirement, and my wife works for a university in Boston.

Then you can read a more in-depth book like The Book On Rental Property Investing by Brandon Turner or The Unofficial Guide to Real Estate Investing by Spencer Strauss.You need to get a firm grasp on two things: the ways to make money with real estate, and how to find deals that match your goals.P.S.

Huge fan.

No maintenance/cap ex, vacancy, PM, book keeping, asset protection, miscellaneous, etc.his actual cash flow when properly allocating for sustained expenses is a fraction of his advertised cash flow.  

I have read the book on long distance investing and still am not too confident to get started.