OSX has nothing to do with ID3 tags. And there have been 400m+ iPods sold with no major ID3 issue.

Just saying that just because it affects you personally does not make it a widespread issue.

OSX as the "package" of OS, iTunes, apps etc does.

You are wrong. This is not a personal issue - it's very widespread and makes a huge number of people suffer constantly:

1. How broken is it: http://www.id3.org/iTunes

2. Other people with problems: http://lmgtfy.com/?q=ipod+wont+play+songs

iTunes is the only mac application I ever tried to use (~5 years ago). That program is a joke. How you can make a program with so little features so complicated to use, I can't fathom.

It boggles my mind that iTunes is as bad as it is. As the main interface between users' desktops and Apples' iOS devices (their cash cows), it should be extremely refined, polished, and usable. Yet it remains bloated, unintuitive, and slow (and I'm on a Mac. I've heard it's much worse on Windows).

They keep trying to push the Album Cover view, yet flipping through hundreds of album covers is an idiotic way to navigate a large music collection. Ping seemed like a half-baked idea destined to fail, and its iTunes integration was so poor. At least they're cutting their losses and yanking that.

I'm not aware of a better alternative though. What program to play, organize, and upload music to your devices do you recommend?

Slightly related anecdote: A number of years back (at least five or six) I noticed that if you made a smart playlist with a time range constraint the "max" time would increase by one second each time you edited/saved the playlist. I sent in a little bug report (through an iTunes feedback form on their website).

Right now I can't check whether the bug still is present in the Mac version, but I can see it still exists in the Windows version.

I may be biased cause I've been using iTunes since I can remember, but it doesn't seem complicated to me.

I've tried a lot of stuff, but nothing can manage well libraries over 10GB. There may be alternatives now, I haven't really looked for one in years (as I said, works for me and I like it).

On Windows, Foobar2000 handles my 77+ GB collection with no problems. It's very lightweight and has many add-on/UI tweaking options.

Aw, Foobar2000! I remember using early releases back when I mostly used Winamp. I'll keep it in mind for my VMs or in case I switch back to Windows.

Thanks!

I've got 14Gb in Zune and its lightning fast on a 5 year old ThinkPad.

To be fair, ID3v2 is a ridiculously complex and over-engineered "standard". It reeks of second-system syndrome, despite not being created by the same person who created the original ID3 format. What was needed was a basic key-value store. What was delivered was a custom container format with an over-complex frame system, a bunch of redundant frame types, an unsync scheme, etc.

iTunes is hardly the only software with issues related to ID3v2 reading/writing.

A company the company the size of Apple doesn't have an excuse to get it wrong. It was poor testing and low quality development.

Have you tried Zune, it does magic to ID3 tags!

I learned the hard way.

http://www.id3.org/iTunes: "It can write 2.2, 2.3 and 2.4. The support in general is good."