iTunes is great software
I can't believe how many people cannot get to grips with itunes. I have used it on windows for years and it's great as long as you follow a couple of SIMPLE rules.
1) Choose to manage the library yourself - so you can maintain your own preferred folder structure for the mp3/AAC files.
2) Ensure you have your tags set up correctly, then all sorting and organising will work perfectly.
When you go to sync, on the music tab there are numerous options for transferring the music across. You can
a) allocate a tick next to an artist, to have all of their music
b) you can select albums on a one by one basis (they are conveniently listed by artist = easy to find the ones you want)
c) create a manual playlist of the songs/albums/artists you want. You can create several of these and sync them all across in one hit
d) the best is creating smart playlists, which are essentially a visual query from the database. eg i want all 4 or 5 star rated tracks that i haven't listened to in 6 months...I also want all music i have added in the last year...I also want all 5 star albums from the 1990s. By using a combination of smart playlists, you can dynamically sync your music within minutes knowing you have all your favourites and/or forgotten and/or new tunes automatically syncing in one hit.
Personally, I use a combination of a, b, c, d above and find it really easy to sync the music I want to my devices without having to manually trawl through 60k songs.
I also use a handful of smart playlists to create my own "radio station" of around 100 random songs that I use for my ipod shuffle in the car. This ensures that only music I like generally comes on, along with a sprinkling of "new/not yet listened to" and "haven't listened to in ages". When I've listened to these, I just re-sync and get another 100 songs that fit the criteria.
I don't know why people find it difficult, either I am some kind of genius or there are a hell of a lot of simpletons out there...
Biting the hand that feeds IT
