Couple other quick hints....
Start small -- get a few synchs under your belt with a small number of songs, 20 to 50. Get a feel for how fast things should run and synch.
Start basic -- dont feel any rush to get complicated SmartLists, they will come over time.
Plan a bit -- when you do start making playlists, look for posts here about how to organize. For example, many people create a base list of "iPod Music" (call it whatever) that might exclude holiday songs, comedy, and songs with 1 or 2 stars (obviously you fill in the specifics of your overall iPod rule). Then base all other iPod lists on that original list. That is just an example, but planning can help you figure out when you want to use keywords in the comment field, or use manual playlists or when to use ratings. For me, I organize my music around "listening activities" -- work out, sleepy, wake up, commuting, cleaning the house, dinner party, office, etc.
Hope this helps!