Our plan is to own $100 million worth of real estate by 2030 and become the premier property management business in all of Indiana.

You'll be selling a house that is worth what comps say it is worth. 

It was hard to find anything that cash flowed enough to make it worth it to us, and I personally prefer to have the ability to manage my properties myself.We decided to pivot into business acquisition.

Mid-term rentals is also a strategy worth exploring, a good book to read on that is "30 day stay" by Zeona McIntyre & Sarah Weaver.  

It seems like I need to check further away from the DMV area.My feelings are if you want “cash flow” you should buy a bond (I really like the tips rate right now) there is next to no reason to buy real estate for cash flow, if you are going to buy you should buy with appreciation in mind, which is not to say that’s the route I’d go, I’ve been liquidating properties to put in stocks and money market funds over the last few years and u just did the math and I’ve come out well ahead, but just to say there are arguments for stocks/bonds, there are arguments for levered appreciation, but the cap rates pretty much anywhere aren’t worth it vs an inflation protected bond, especially since a 3/rd of inflation is real estate anywhere, you could get “cash flow” and inflation protection much easier through a tips.

In fact, I’ve learned that they owe more than the house is actually worth.  

A friend of mine recently got a $2M umbrella policy for around $300 annually by bundling it with home and auto insurance; it’s worth exploring.Out of curiosity, are you primarily investing in residential properties or venturing into commercial spaces?

Even if you rent at a break even or slight loss, if you could have 3 years of rental income offsetting your mortgage while realizing 3-6% appreciation, could be worth it, especially if you think appreciating for this area will exceed national averages.

Remember, the notion of amassing wealth without investing is a dangerous myth perpetuated by self-proclaimed experts.

2) I think it is important to remember a key part of the VA loan entitlement.