So I'm thinking of getting an iPod.

Why? Because every player that I look at looks good at first but is soon exposed as having some kind of fatal flaw*. iPods have generally very well made and work properly, but have one huge Against, you have use iTunes...

Against:

• You have to use iTunes. I hate iTunes. It gets worse with every update.
• Expensive. 8Gb Nano is $200, 8Gb Touch is almost $300.
• I'm clumsy. I don't like the idea of dropping such an expensive device. I need my MP3 players to be either cheap or mega-robust.
• iPods won't play FLAC, or OGG, or a whole bunch of other file formats.
• Thief bait.

For:

• iPods have excellent sound, are well built, have nice interfaces, have good battery life and Gapless playing...
• ... and I've yet to find any other non-iPod player that I like.
• You don't actually have to use iTunes. You can use various third party tools to get your music onto your player. However, you still can't just copy music onto it like almost every other player on the market. Also, the third party tools break on every firmware update. And if I wanted to buy apps (see next point) I'd need to use iTunes.
• I could use the iPhone/iPod Touch Music Collector collectorz.com application to have my whole music collection database on hand for those times I wonder, "do I already have that CD?"
• I could use the iPod Touch as a teeny tiny netbook at home to search the web on it (with Wifi) and play games on it.

* For example, the Sandisk Sansa Clip+ which sounds perfect for what I want (gapless playing, replay gain, plays zillions of formats, you just copy mp3s onto it without the need for software, very cheap) but it is only available in the US and apparently has a bug that plays 44.1hz (CD quality) slightly slower than it should, something that would drive me mental.

[An updated version of this post with the dates reversed so newest is at top.]

I do this because I need a new media player and I'm actually thinking of taking the plunge and getting an iPod Touch... to be explained later.

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A history of portable music.

2008 - iRiver e100 8Gb with FM, voice recorder, video, colour screen and ability to play FLAC files
[Initial review] Plagued with firmware bugs. Crashed when it hit a file it didn't like. Very noisy buttons. Never really used the video beyond some initial experiments. Never used the voice recorder. FLAC playing was excellent, but in reality, copying such large files over USB 2.0 was too time consuming so usually converted to MP3 first anyway. Dropped many times. Eventually the headphone socked started crackling and the left ear stopped working.

2006 - SanDisk Sansa m240 MP3 1Gb with FM and voice recorder
Took normal AAA batteries which was really useful when caught out of juice. Used the voice recorder once. Screen was small but usable and accurate. The plastic on the hold button broke eventually but it still worked, and the plastic cover it came with yellowed and eventually looked revolting. I still have this player, it works fine as a backup when required.

2004 - Panasonic Discman SX418 with MP3
No radio, but MP3 playback from CDr. Worked fairly well for a year or so but didn't survive being dropped a few times. Lost the clip that kept the lid closed so it was kept shut with a rubber band for a while. Discovered it was scratching my CDs. It's in the bin. When it broke I went back to my 2000 player.

2000 - Panasonic Discman SL-SX279V with FM
Purchased in San Francisco's China Town for around AUS$200. Very well used over the years. The anti-skip started to go eventually. Never really played burnt CDs very well. FM was a nice bonus. Has been dropped many times. I still have it but I'm unlikely to ever use it again.

1999 - Sony Minidisc MZ-R50
Used to record many a gig and every Walken jam and gig since the very beginning. Never really used for listening to pre-recorded music though.

1999 - Aiwa Recording Walkman (tape)
Used to record many a gig and a few solo/Walken jams. I still have the box but the Walkman has gone AWOL.

late '90s? - Sony Discman
A gift. Well used and loved. Antiskip sucked. Played burnt CDs without a problem.

mid '90s - Sony Walkman (tape)
I remember when it got older it would play tapes too slow. I remember I got so angry at it I threw it against the wall. It broke. Dad fixed it. Dad rocks. I suck.