Here's my issue with iTunes,
1. iTunes can't play the thousands of illegal songs that I may or may not have collected over the years.
Your problem for not choosing a standard format like MP3, which iTunes can play and is the most popular format for illegal songs, hands down. This one's your fault.
2. When I decided to sell all 1000 of my CDs many years ago, I used WMP to burn them all. It defaulted to WMAs which means I'd have to convert everything to MP3s and lose quality.
Again, your fault. I won't lie, I have illegal songs I ripped from CDs I didn't own 10 years ago still. They're MP3s. They worked fine then, they work fine now in iTunes.
3. I have spent 7 years naming songs the way I like. Because I'm a huge Jazz and Classical fan, all of my songs are labeled Song-Artist (because there tend to be more covers of the same song than there are in Rock or Hip Hop). So I can look at my collection and see instantly that I have 10 versions of "Misty"--each one my a different artist. I can tell that I have 5 versions of Beethoven's 4th Symphony.
So, you've named all your files but not tagged them? Guess what: 10 years ago I was tagging my files with ID3. It's been upgraded and can store more information since 2000 or so. You have no excuse for relying on file names for organization. Not to mention that you could sort your entire library by song name in one click, or even search for a specific song name, and come away with the exact same information.
4. I have spent the 7 years organizing music the way I like. I have about 13 different genre fields (iTunes has about 10000...and some of them aren't even genres). When i go to my Bossa Nova folder, I'd like to see all of the bossa nova songs that I have....not What iTunes thinks is Bossa Nova...but what I KNOW to be bossa nova.
What? What are you even talking about? "What iTunes thinks is bossa nova?" iTunes doesn't THINK anything. It just displays what YOU'VE STORED in your Genre tag. You control that, not iTunes. If you tag your files, that's how iTunes will organize them. It doesn't tag anything by itself (unless you're talking about stuff you buy from the iTunes Store, which you can change).
5. I don't want 5 different Stevie Wonder folders. stevie wonder, STEVIE WONDER, Stevie Wonder & John Smith, sTeViE WoNda...etc. If I absolutely absolutely must view my songs by artists, I want there to be one Stevie Wonder folder....one Michael Jackson Folder....etc.
Well then it's a good thing that Mac OS X's file system (and iTunes) isn't case-sensitive by default. Of course, it's also trivial to change many tags at once in iTunes by selecting many files and using the Get Info command. Also, you can easily turn off iTunes' file/folder re-organization and it won't touch your current layout. I think that's pointless, since part of the APPEAL of iTunes is that a database is way more flexible and can do exactly what you want as long as you tag your files correctly and you no longer have to worry about file/folder placement, but nevermind that.
6. I don't care for proprietary submission. I like to play what I want to play...organize what I want to organize.....and use my computer the way I want.
So, again, don't let iTunes organize/rename your files. It's an option, un-check it. That doesn't excuse what seems to be mostly your bad tagging habits, but we'll let that slide. iTunes is just a database of your music. It's exactly as organized as YOU make it, via tags. Everything you want can be accomplished, you just need to get out of the "manual file/folder management" style of thinking and into the "tags/metadata" style of thinking. It's a lot more flexible in the long run.
I'm all ears. I'm not a Mac or iTunes hater. But I think that I use, burn, and listen to music very differently from most. With Media Monkey, it shows me my MY MUSIC folder which has the 10+ genres inside. I click on Vocal Jazz and I can see all of the vocal jazz tracks contained within. Brilliant.
I don't see how anything you've said CAN'T be accomplished with iTunes—besides the large proportion of your collection stored in an unsupported format. Sorry to be harsh, but it sounds to me like you barely even LOOKED at the program or its capabilities before deciding it wasn't sufficient for your needs. Tag your files, turn on browse mode, turn off the "keep my iTunes music folder organized" option, and move on.
I cannot stress enough:
a well-tagged library is crucial. Of course, that's my opinion regardless of what player you use, but with iTunes it's the starting point.
Well, that and "not using competitors' proprietary formats."