He also owns propwire.com which I currently have a free account that shows the history of the property and allows Skip trace for a fee. 

You can get 2 houses in B areas in Montgomery for $250,000.  125k house will rent for $1,050 -1,150.And, second lowest property taxes in the nation behind Hawaii.

Out of money and options, he licks his wounds and lets it go for back taxes. 

Seems like it may be better control of your money then SDIRA and less fees.  

Also, even though we make negative cash flow, since its big house and income from house is a lot we had to pay more taxes. 

Triple net leases (NNN) are standard, and they cover taxes, insurance, and maintenance.For your 1.8-acre parcel, if it's zoned for auto work and sales, you’re good to get started.

In Washington County, Maryland, if my Lease Contract says all charges owed are considered rent, if my tenant paid their base rent but not maintenance fees and water bills owed, can i file against the tenant for failure to pay rent?

When you buy a tax certificate for vacant land in Alabama,1) Do you have to wait 3 years to get the tax deed and in the mean time have no right to the property2) Do you still have to take possession of the land after getting the tax deed.

My question is: how is capital gains tax figured?

First time I've heard of this method but certainly sounds creative - The end buyer is probably likely to still come up with close to $100k on transaction costs with the double dipping of loans and other processing fees most likely.