I'd have to say I'm more excited than ever about my music since getting the iPod.
I find it really helps to take the time and organize your music properly, adjusting the info for each song when needed, and having a variety of different playlist options available. I took a long, rainy weekend of last year to do this with the songs I already had. And now, the one thing I immediately do with any song/album I download or import is change the "genre" in the info setting (and year, if it's not accurate -- usually only a problem with "Best Of" albums or reissues). I find the pre-assigned genres given to songs way too limiting or incorrect, and I either change them to how *I* see them, or add more if I feel they fall within more than one genre. Then I also assign a "mood" to them, like HAPPY, LAID BACK, HARDCORE, ENERGETIC, SAD, STRANGE, PEACEFUL, or whatever.
And from there, I can then make hundreds of different smart playlists using any combination of one or more of those genre/mood keywords. So I literally have a playlist for any kind of mood I'm in. And since I didn't handpick the playlists myself, and I'm using the power of smart playlists to choose the songs for me, I'm often surprised by what I find sometimes (I of course ALWAYS have it on shuffle mode). So I'm getting songs to fit a particular mood I'm in, but not necessarily knowing which songs to expect -- it's a really cool way of listening to music.
Some more fun smart playlists to make are ones done by year. Pick the year of your graduation, and suddenly you're taken back to that time of your life. Or go back further to your childhood. Or just flashback to 2000.
Definitely take advantage of the power of iTunes' many features! And if you're STILL bored with your music, maybe it's time to just get more. Use the handy features of the iTunes Music Store and browse the "just for you" section (which recommends music based on previous purchases), or the even more useful "listeners also bought" feature -- which has made me discover dozens of new bands that I now consider some of my favorites.