I paid thousand of dollars to do tax planning and I got two meeting so far with not tax planning, just chatting.  

DealMachine is a powerful tool for real estate investors, especially for finding off-market deals through driving for dollars.

In fact the developers formula that I use to come up with a max offer that was taught to me by a very successful land developer is .4x(Sellout Market Value - Development & Selling Costs) Basically, it's 40 cents on the finished dollar less costs.  

Every little fee adds up to big dollars. 

In inflation adjusted dollars, this likely is closer to 15 years to recover the $450k.  

Rent is already in line with the market on all 3 properties and we have a few hundred dollars of cash flow.

I currently have $350 dollars that is missing from a chargeback reversal from a tenant that has a document case with Amex and a statement to prove the money was sent back to me. 

When I used to have RE Broker in my title ( I still have the license just dont practice) I would get folks pinging me about Vegas about once a quarter or so and I would hand those leads to my Daughter  she made some pretty awesome connections from a few of those folks that bought multi million dollar homes..

So in reality you are ALWAYS gambling in the stock market, yes, even with those big names that seem inconceivable to every drop and ESPECIALLY with those because most are so shocked and in disbelief when it occurs that it's only realized after your left with pennies on the dollar because you waited out a recovery that was never coming. 3rd: MATH and leverage.     

But if you have a self-directed IRA or 401k, keep this strategy in mind, as it could potentially save you hundreds of thousands of dollars in taxes.