Calling ex-Windows users - how do you survive on a Mac?

Question

I am curious what recent Mac-converts who have used proper Music Management software on Windows do now? I understand that newbies who have only used the iTunes application (even on Windows) are quite content with iTunes, but what about those who got used to proper music management software such as Media Monkey or WinAmp?  I realize that if you only buy stuff from the iTunes store you are again probably fine with iTunes (it seems to be primarily a front-end to the iTunes store), but what do other people do?
Is there any alternative music management software on the Mac? Is SongBird any good?
Do you just spend your time endlessly converting files so that iTunes will read them (losing quality on the way)?
How do you maintain ID3 tagging?
How do you share music freely given the iTunes policing restrictions?
Have you just given up on music while you have a Mac?
Do you run a VirtualMachine with a Windows partition so you can run a Win music manager? This worked well for me for a few months, but the Mac crashed so regularly (every few days) with VMware that it became unworkable
I realize there are a number of external applications that fix some of iTunes major technical shortcomings by enabling syncing to non-Apple devices (at more costs), but the few I've used are pretty flakey (no option to sync to SDcards yet). The lack of video support in iTunes (apart from 1 or 2 basic formats) is forgivable as I just want to manage music. Then there is the interface and functionality shortcomings:
No 'now playing' queue window
No customization of look & feel
No lyrics viewing
Can't export M3U files configurably for Windows
No navigation/management of files on disk (and yes, I do not let iTunes manage the files - as if)
Loss of track data after importing or overwriting (album art a total mess, probably due to lack of ID3 tagging)
Inability to change multiple tracks tags
No flexible/editable get album info queries (only looks at iTunes store)
Lack of add-ons to fix the holes (and I have seen some of the proposed add-ins like Dougs AppleScripts, and am unimpressed)
I could go on and on
The bigger problem is that a Mac doesn't really work unless you use iTunes. It seems all Apple solutions demand iTunes. So, I can't have an iPhone, no iPad, no AppleTV, no FrontRow, no use of music in iMovie or iPhoto, etc. But using iTunes means I lose 20% of my music (non-MP3 files), can't synchronize freely, can't share freely (I have kids with numerous devices), no lyrics, no add-ons with external artist links (youTube, upcoming concerts, etc.) and have a drastically reduced user interface experience (without peronalization options).
It is now almost 1 year since I got my latest Mac. After 6 months of face-palming, the arrival of Microsoft Office 2011 finally meant I could use the Mac at work (finally a working email client that can send more than 1 attachment in MS exchange environments), and there it has stayed. I don't have a massive collection (20,000+ tracks), but the inability to manage music is a show-stopper for home use of a Mac.

Answer 1

Your correct for this forum is for using iTunes and other Apple products.
Anyone changing from one platform, especially using proprietary formatted data, is going to have issues when you completely change operating systems. The Mac OS has been a leader in the fact that it includes and supports more international standards than any other OS. At times it may seem like the Mac OS is inflexible, but it is trying to get you to stick to standard, which in many cases you can completely ignore.
Maybe the Mac OS isn't for everyone, especially someone who wishes to have an active role in everything that happens on their system and devices.
Myself, I can't see manually moving songs on my system and on/off my devices. I simply let iTunes playlists and smartlists do that for me, all while making sure I still keep free space on my devices.  The recent announcement of the new, and free, iCloud service and it's integration with Lion (10.7) is designed to make syncing and updating even more hands off for users. For me and most of my customers, this is very exciting.
While there are some limitations that you mention that are true, (M3U, ID3 and loss of track data -only because of a non universal fixed standard for this data), most of your complaints are only partially true, if not completely wrong. Without spending an hour replying to all of them, I'll pick one, iCal.
My iCal (and Calendar on my iOS devices) tracks/syncs with 14 different calendars. Of these only 4 are created within iCal (one being ToDo). 4 come from 3rd party applications on my computer. 1 is Birthdays that are automatically imported from my Address Book. 5 are free subscriptions from 3rd parties that include Holiday, Seasonal as well as solar/lunar data, my favorite NHL team schedule and my Facebook Events. I also subscribe to my local Apple Store events as well. At my last workplace we use Google's software for all of our email and scheduling. I used 2 different calendars that we synced within iCal and my iOS devices. That is synced, not subscribed, as I was able to make new appointments and change existing ones from all of my devices just like any other calendar that I have control of.
I suggest you ask for help in what you need in converting in your OS switch, or attend one of the free workshops at an Apple Retail Store, or check out the tutorial videos that are here in the Support section of Apple.com. You don't need to drink any Apple Koolaid, but rather be open to a different way of doing things.
Why does what I say matter? Maybe it doesn't. I'm just a all MacOS/iOS user who switched years ago, but is the person that thousands of MacOS, iOS, Win 95- Win 7, Blackberry and Android users go to for help, with their over 600 systems for close to a decade. Yes, we used MS Exchange servers and send more than 1 attachment at a time as well.