I let him stay in the homes he was working in, threw him money for food and gave him some cash when the house was done, but it was primarily room and board he worked for.

Can they get to food shopping easily?  

Some we have put into stocks, but we are really at a loss at how to invest the rest.  

But again you aren't flipping just food for thought.

Do you then sell for a loss or do you turn it into a rental?   

Just food for thought :)

Plane tickets, hotels, car rentals, food, etc. all add up.

I'm a retail net leased investment broker based in Los Angeles, and I specialize in single and multi-tenant retail properties leased to the national credit "daily needs" tenants ranging from the top grocers (The Albertsons Companies, The Kroger Company/Ralphs, Wal-Mart Neighborhood Center, Trader Joe's, Sprouts, Whole Foods), to the drug stores (Walgreens Boots Alliance/Rite Aid, CVS), to the discount retailers (Dollar Tree/Family Dollar and Dollar General).  

This lends to going down the path of possibly providing the tenants with financing, installment contract, disguised sales, delayed closing transaction, equitable interest, refunds, lawsuits, loss of profits... etc.

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!)