The most important part of my routine is to wake up on time (usually anywhere between 5 am and 6 am). I've tried various setups and each one failed for different reasons.
First, I setup Winamp as an alarm clock (using the WinAlarm plugin), left my computer on overnight with the speakers plugged in, and woke up to the Winamp playlist. Nothing more wonderful than waking to energetic music. Unfortunately, I would sometimes forget to plug in the speakers. Also, leaving your computer on overnight puts unnecessary wear-and-tear on your hard drive.
Second, I tried getting an iHome iPod alarm clock (something similar to this model but older). That was pretty expensive as I had to buy both the iHome system and an iPod. The iHome worked fine but it had terrible sound quality.
Then I went back to a conventional alarm clock. Unfortunately, I just can't get up to the sound of beeping. I get up, shut it off, and jump back into bed.
Finally, I did some research on better iPod sound systems. I found the Altec Lansing iM600. Altec Lansing has a reputation for making good speakers and this particular product had very good reviews on Amazon. So I coughed up some more cash , got the iM600 and plugged in my iPod Nano. It works perfectly and I can even setup multiple alarms using the built-in "extras" software on the Nano. I have one alarm that plays the Barenaked Ladies's song "Who Needs Sleep?" at 9 pm as a reminder to get to bed. Then I have an alarm at 5:30 am which launches a playlist of rousing country, bluegrass, and alternative songs. It works.