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? No you will need alot of different items, most have been listed here time and time again. Do a search in the reloading forum for "getting started"
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. What ever press you get, just get the standard 30-06 FL dies that go with them, unless you are shooting a pump or semi auto, then a small base die is recommended.
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. From my experience theres not alot of difference between the average brass companies. Flash hole shape is the difference. IMHO Winchester has some of the best low end packaged brass out there. Remington has alot of quality issues such as poor packing, and bent rough shaped brass.
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. I would personally want to choose which primers I am using.
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. A tumbler is the way to go! It is relatively easy and it does all the work. You will want to clean your brass so you can see if your brass is damaged and ready to be discarded.
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.. [:'(] There are several ways to determine your seating depth one is a Stoney Point gauge the other is the old fashioned way of using a fired casing and putting a bullet in the neck and pinching it a little. Then chambering the casing and measuring where the bullet stops this is the base line from which you decide how far back to seat. Some guys start at .010" of the lands Ive seen .090" off alot depends on cycling through your magazine also. If you are not comfortable "measuring" and "math" you may not want to get into this, reading and using a good set of calipers is a must for doing this stuff.

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

Most all of these questions can be answered by buying several good reloading manuals and reading the intoduction to reloading segment. Not to sound judgmental but with the questions you askedyou should do this way before you ever press a bullet.