I've been doing home based business for a long time. It started when I was in NY. I became a scuba instructor. Later I turned that into commercial diving work which paid better and took less of my time. In '93 I finally quit my full time job, actually got fired when the company went out of business. So after a few months of job searching, I realized I'd be better off expanding a home based business doing what I enjoyed full time. I'll never go back. The trick as you indicated Van is figuring out what you want to do.
You have divided it into a different approach from what I consider. You are looking to work for a boss but at home. I have never done that. So no advice from me.
Here's something you may consider doing- How about quick turn real estate service. You buy up a distressed property cheap and sell it fast to another investor. The biggest problem these investors have is finding a property to buy, not to be able to sell it. Maybe you don't have the cash for that now, So, you make a job of locating properties that are on the market cheap, do some photos, write up a short spec sheet and contact information and sell it to an investor. I can give you more details if interested in how this works but it is a way to get your foot in the door, learn the ropes before doing your own buy sell to make the big bucks. You are your own boss and you can sell the product on two levels, the info pays $50 and if he buys the property you get $500. Think this sounds crazy? I know a guy here in Jacksonville who has been working with people with this program for the past 10 years. As I recall, he pays out a $500 commission for 1 in about 50 properties so it becomes a numbers game. He stopped doing the search himself and relies totally on his scouts. His scouts are mostly college kids and housewives with a digital camera. Oh well just an idea.