I was in the same boat. I had a Zune HD, and it was a very underrated hardware/software package. Probably a good example of a superior product that was a victim to timing, marketing, and other forces outside of the product itself.

It's biggest problem was timing -- launching less than a year before the iPhone was a huge problem. The market had moved on from the entire dedicated MP3 player space before the Zune had a chance to find a market and iterate on the product to refine it.

I think the biggest problem was that nobody took it seriously, and I'm not really sure why. It was easily as good, if not better, than the iPods of the time. I definitely don't think it was an issue of timing though. the iPhone's capacity at launch (8GB) was a joke compared to dedicated players at the time. And music streaming services weren't all the popular. Plus even if they had been, it would be a year until we saw a 3rd party app store on the iPhone.

>I think the biggest problem was that nobody took it seriously

There was that one guy, who got the tattoo...

Jesus, that guy. He's lucky it's a pretty neat-looking symbol. So in 10 years when nobody recognizes it he can play it off as some obscure video game reference.

Not just one. And considered changing his name to Zune too. He seemed to regret it though. http://www.wired.com/2009/09/zune-tattoo/

It was too little, too late. They were roughly as good as a well established option, with a better ecosystem. There is nothing compelling about that, and as noted the dedicated player was about to get its lunch eaten (not that anybody knew this).

I think its biggest problem was that it had wifi, but didn't have a web browser. Then six months later, along came the iPod Touch ...

I don't know if that's true. The first few iPhones were very expensive unlocked and on contract, required signing up for a $70-$100/month phone plan, which was close to double what dumbphone users were paying. The iPod Nano, iPod Touch and iPod Classic saw updated versions each year, slowing down only once iPhones and Androids became mainstream and replaced dedicated music players.

The original iPhone was 400$ without contract (it was locked to AT&T though). However, it could be jail broken by simply going on a website using the built in browser. Unlocking it wasn't much more complicated too (within the launch week, you could unlock it with a turbo sim, and couple months later software unlock were released).

I got an iPhone 3G in AU on a 2 year $40AUD/Month contract.

At the time, this was almost half what I would have paid pre-iPhone. Before the iPhone, I would have had to get a normal contract, plus a data add-on. Monthly cost was close to $80AUD.

Didn't a similar bundling of services at relatively lower costs happen in the US?

Still more expensive than call and text only, but still not that expensive.

the software was abominable. The zune ran a version of MTP that was proprietary and so could not be used on older versions of Windows or Linux... while ipods worked beautifully on Linux.

Just getting Music on the Zune using the desktop software was an exercise in pain.

Agreed, entirely. I adored my original Zune, as far as a piece of hardware, it was amazing. Cool look, big color screen, heck even an FM tuner. It was ahead of its time. The software on the other hand still gives me nightmares. It crashed all the time, would constantly lose large chunks of metadata I had meticulously entered, would randomly freeze while loading music... it was the weak link in the Zune chain.