I don't know where you got the info about the indie labels, but I'd recheck it or get a better source.
I got that (a couple of years ago) from a marketing manager at Inception Records, who claims that ITMS refused to carry their music unless they were allowed to add DRM to it. Possibly he was lying, but I assumed that he knew what he was talking about.
Second, if I understand it correctly, you're pissed because you can't just take your iPod and download all of your music onto any computer you happen to come across.  You want it so that everytime a friend comes over you can just plug his iPod into your computer and steal his entire library.  And you wonder why companies are pushing DRM?
First of all and once again: Randomising the file names does not constitute DRM. You can put an iPod into disk mode and copy the music off onto your friends computer, and play it perfectly happily, assuming there is no actual DRM. Of course, it might take a while to re-name everything sensibly, but it provides absolutely no copy protection whatsoever.
If those tracks 
are DRM'd, though, then the publishers can prevent them from playing on unauthorised hardware, and coping music between computers becomes futile.
Second: I do not have an iPod. The DAP I 
do have acts as a UMS device, and I can drag-and-drop directories on and off it as I see fit. I also have no DRM'd music, as almost all of it has been ripped from CDs, with a few titles bought from Amazon, or other DRM-free source. And yet, I've managed to avoid the temptation to "steal an entire library". I have no desire to steal music from anyone, and I don't want to infringe on the rights of the copyright holder, but I also want to be able to exercise 
my rights to the music without Apple (who after all, are not the copyright holder and do not represent them) telling me that I can't do it that way.
Do I wonder why companies want DRM? No, not particularly. But I do wonder why no-one has ever done any studies to find out if their DRM is actually doing any good, or just costing a lot of money and driving even more people to pirates. I suspect the latter, but we really don't know.
But this is irrelevant, because the issue wasn't about DRM. It was about a bizzare file structure system that does nothing to protect copyright, but is specifically in place to encourage people to use iTunes to manage their iPods.
The point is that you suggested that not being cross-compatible with other companies' products was a failing for Microsoft, but when Apple put deliberate roadblocks in place so that owning one product pretty much requires you to own other Apple products, you go into some bizarre tangent about DRM being forced on them by record labels.
The first couple of generations of iPods could only be connected to a computer via firewire. Is it just coincidence that firewire ports are standard issue on Macs, but not on PCs? Or was this also forced on them by the labels?