A year ago I was where you are. My strategy was to spend the least amount of money possible until I could determine:
1. That I could actually successfully cast bullets.
2. That I enjoyed doing it.
I started with
1. A used Lee 10 lb bottom pour pot I bought off another caster.
2. Thermometer bought used from the same caster.
3. Lee 2-cavity mold
3. Lee Lube and Sizing kit
4. 50 lbs of lead ingots made from reclaimed wheel weights bought from another caster on the castboolits forum.
5. Spoon, cake pan, disposable roasting pan, and a couple kitchen towels from the dollar store.
6. Goggles, welders apron, and welders gloves from Harbor Freight.
Some observations:
1. The 'customer satisfaction rate' on Lee's 20lb pot seems to be much higher than the 10lb pot. I'd get the 20lb pot if I were buying it new. (I have since upgraded to an RCBS Pro-Melt but that's in an entirely different price range).
2. As soon as I knew I could successfully make boolits, I bought a 4-cavity brass mold from Tom at Accurate Molds. It has been money well spent.
3. I cast and shoot enough (5000 rounds per year minimum) that I plan on buying a Ballisticast Mk VI for sizing and lubing.