1) I'd recommend you start with a single-stage press, learn the basics on that. If you decide later on to go to something that produces rounds faster, you can always sell it. I load for F-class competition, so I'm more interested in small amounts of precision loads than I am in producing tons of ammo. Check the EE for basic kits, or check out someplace like the Wholesale Sports website for prices.
2) It's easy to learn. It isn't rocket science, but it does demand your full attention at all times, and you must know what you're doing. How do you learn that? By all means, get a manual or two. Try "The ABC's of Reloading" for starters. Here's a basic overview for you, courtesy of RCBS:
http://www.rcbs.com/guide/printsteps.html
If after reading that, it looks like it's too much work, or too finicky, stop now, you're not ready for this.
The best advice I can give you for now is a) get a friend who reloads to show you how it's done, and b) start reading this reloading forum. Go through previous threads, make notes, make a list of questions, try to find the answers, when in doubt, ask a question here. We're nice folks, we hardly ever bite.
3)
http://handloads.com/calc/loadingCosts.asp
4) See 2) above.
Again, you can do this, provided you're willing to take it seriously, not cut corners, and do your research. A year ago I knew nothing about reloading, today I was at the range working on load development for my target .308 (testing different powder weights to see which one gives me the tightest group).
5) You're welcome, and welcome to reloading!
