Jeff,
Pace yourself, buddy. It takes MANY years to build up to the workshop of your dreams, and for good reason. As you learn to make do with what you have, you learn a lot of basic skills. I have more than once bought tools at a bargain from someone who bought a ton of tools all at once and thought that would let him make fantastic furniture the next weekend. All it did was left him frustrated and disappointed.
Machines don't make the woodworker, they help him. Start small, get good with what you have, and then let your projects steer you to where you need to go. If you're doing small boxes and turning pens, why would you need a $1000 tablesaw? You could rough your stock on a bandsaw or even use a circular saw, or even a $200 bench tablesaw.
Look around for older tools in your area. Find a good used bandsaw or tablesaw, learn how to tune it up. Save up and buy 'quality' tools, you're young and have the time to hunt out the real gems in classifieds and on Craigslist. You will be amazed at what is available. Remember when you deal second hand, all prices are negotiable, but be reasonable. Almost every woodworker I've bought a tool from has been willing to sit and talk about what they've made with that tool, and how to get the most from it, and I think they're generally sad to see the tool go. A couple just want the albatross gone....
If you're going to try to sell stuff, make sure you can sell things first! Nothing hurts more than having a bunch of craft show merchandise sitting unsold on your shelves in your shop mocking you on the waste of time and resources you put into them. Make a few boxes the hard way, see if they sell, then you can figure out what tools will make it more profitable for you to meet your demand.
I admire your ambition and drive, but would hate to have you make some of the mistakes that I and others have made already. I don't mean to ramble on, I hope that I've given you a tip or two you can use.