I have used Macs since the 80s and iTunes since it first showed up. I love iTunes for Mac, generally more with each version, but I do have to say the syncs to mobile devices have become sort of kludgy in some respects as time has moved on, particularly if you have multiple devices, multiple iTunes libraries, keep movies on external disks with a separate library on your computer, etc. Plus I'm not thrilled with the options offered for automatic sync of stuff.
I think that's one of the reasons Apple is moving now to the wireless sync and cloud storage of purchase history.
Anyway currently I use all manual syncs because I never want "everything" and don't see how the choices for automatic syncs necessarily match up with what I would pick. Like for podcasts. So I just do everything manually. It takes some time especially when I decide to wipe one of the pods and start over from scratch, which I do periodically.
I'm a big enthusiast of foldering playlists in iTunes. It reduces clutter but lets me save playlists I've liked in the past and might like to rotate back onto an iPod now and then.
More on sync: I have not liked that "transfer purchases" didn't come with an option to say which ones. There can be good reasons not to transfer all your purchases from an iPod to the main library's itunes data. One of them is if you keep movies on an external drive and don't happen to have the drive mounted when you mount the iPod to sync to your library. The software doesn't see the iPod's flicks present on the iTunes side of things, so if you want to upgrade the iPod software, it starts carrying on about how you haven't transferred all your purchases. Makes me nuts! I end up deleting the darn movies and figure I'll hook up the external drive later and copy them (or a new selection) back to the iPod after I do the upgrade. Takes time, ticks me off, makes me want a notebook with a 2TB drive and do away with the separate drive for my purchased movie data...
On the bright side, going forward, i am excited about being able to reference my purchase history via the cloud. I back up my stuff but am always concerned that I'll forget to transfer the occasional purchase made directly onto an Ipod or iPhone. I would not be a frequent wireless sync user since my DSL is not fast, but it will be nice to be able to get the odd one or two tracks redownloaded to my main machine sometimes.
As far as iTunes itself is concerned: I have found it wonderful to use --especially as software bundled with the price of the OS, for heaven's sake. When I think back to the price of some of the much less broadly useful software I've bought... wow! I make lots of playlists, rework how I select or sort displays of stuff in the browser 20 times a day, love to option-shuffle playlists and then save that play order if I like it, use smart playlists all the time on the main library and on iPods as well, think on the go playlists are fun timesavers. The Genius feature gets better and better, that really is wonderful. I have a bunch of older but still useful iPods and lots of different playlists and can folder separately in itunes the playlists I like to use for each one.
Sure it takes a little while to explore any software and try different features. For me it has been worth slowing down enough to do that with iTunes. I now maintain separate libraries for classical music and operas, versus my other iTunes library with everything else in it. I use the option-open command and choose the library I want to use when I launch the iTunes program. This works pretty well for me although I guess it could confuse or annoy some people. I like it because the way I search for, sort, view and listen to the classical works is very diffferent from how I use my other iTunes data. So having multiple libraries seemed like the only way to go, I'm glad I don't have to keep them in separate user accounts.
TV, as well as stream to 2 
