I was as tentative as you when I first rooted my OG Droid. "What if I screw up? skip a step?" and all that. It really is hassle free and painless. Almost like a shot...I guess...just not as quick
As Capt said, read. Understand it and once you feel comfortable just go for it. Just make sure you follow each step and make sure you have everything necessary BEFORE starting the process. Like Capt, I used sbenson's method and it was easy. If you aren't comfortable yet, think about it a couple days. Think about the benefits of rooting vs leaving it stock. If it seems like it isn't for you, step back into your comfort zone and don't root, leave it stock it's still a great device. If you ever go back to pondering root, the EDUs will always be there. And just remember, we're all here to help you out.