- Should I go back to school and obtain an Associates degree in Real Estate? 

Is that process too complicated, yes, but there is nothing in this decision that will prevent a tax sale purchaser in MD from reselling at a profit after obtaining the property by foreclosing the right of redemption.

Why couldn't the officers in RAD obtain financing for their primary home from traditional lending sources?

You can surely buy cheaper properties and obtain the same debt pay-down, but now you've got 5x the head-ache, so right asset class is more about efficiency when it comes to debt pay-down.Tax shielding is similar concept in that more expensive properties directionally give you more building basis to depreciate, which means less net income to tax.

There are alot of real estate strategy out there which will allow you to obtain a piece of property unconventionally. 

Leverage technology early and put everything in the cloud, so you can access info wherever you are.Make sure to get properly licensed and obtain E&O Insurance.

While they were good about obtaining a refund, etc., it still took time (and all communication is via chat or email, for me, chat was easier).

If you own more than 20% of the entity when the loan is obtained, most lenders will likely require that you PG the note.

Obtaining the type/quantity of land we would like to settle on at this point in our lives is not really feasible (i.e. several thousand acre cattle ranch).

We didn't because we needed to provide POS in order to obtain our STR permit being that previous owner had a permit on the property already.