There are ways to minimize your Self Employment Taxes, and you should speak with a competent CPA to outline the other aspects of your life so that they can make a good recommendation for you.Please note that there is no one cookie cutter approach to this.  

Health insurance is only one aspect of your "freedom" plan.Tally your overall expenses: Housing, food, clothing, insurance, medical expenses (those babies aren't cheap!)

Don't get too caught up in the complicated aspects of REI right now, your buy and hold plan is a good idea.

If a commercial broker only does real estate, but their client wants to sell their business too, does the agent work with attorney to cover the sale of business aspect?

As for the maintenance aspect, there are a variety of ways to structure this as well-- Have the seller resolve the issues first, or negotiate low terms in exchange for you to resolve the issues, or pass along the issues to the tenant/buyer in exchange for terms favorable to the tenant/buyer. 

This will entail, making application with the property address being listed as TBD, but you and the lender can have a meaningful conversation regarding all aspects of your loan request and your credit profile.

Leads me to believe they do this with all aspects of REI learning.

Starting out is a critical time to establish how you're going to manage the property.

I'm not sure on the technical aspects on the code for leaving it that way.

I am eager to learn and open minded to all aspects of real estate, but I am primarily interested in small multi family homes.