I have questions and can't quite make up my mind till I get some of them answered. So any advice, input etc, would be ohhh so nice.

I'm looking at the Lee Anniversary kit w/reloading manual, low cost and most people seem to like them for beginners. This is great less then $100 and I'm off and reloading.. or am I?
1. Dies, I'm looking at reloading .30-06, and eventually if this works out also .243 and .40 S&W. Just talking about the .30-06, which dies would be best for a fellow using his personal fired brass? Figured I'd start there before looking at fresh never loaded brass. I'll probably only be loading about 50 rds a pop, if it matters.
2. What is the main difference in brass makers like Rem, Federal and Win? I mean, looking about there is normally a $5 per 50 price difference, mostly the Federal seems cheaper cost.
3. When and if I decide to buy brass, which would be best for a newbie, primed brass or unprimed? I imagine one less step would be great, but I don't know if the quality is that different then doing it myself where I get to pick the primer itself.
4. Cleaning brass, I notice the kit doesn't make too much mention of this step and I imagine after a few firings it will become a REAL concern. So what's the most cost effective way to do this? I've read about tumblers, media etc., but I want to keep costs down i case I decide to bail out on this.
5. How does one decide what bullet seating depth to go with and will the instructions explain this? I think I read somewhere about dies you have to adjust this setting before getting to carried away.. and it sounds like it involves calipers and math.. [:'(]

I reckon the rest like powders, bullets and what not will depend on the load data and what my rifle likes..