iTunes is still one of the best ways to build a lossless music library on Windows. It rips CDs automatically, organizes your files, and syncs to iPods. I have five separate libraries on one PC - one for me, one for my wife, one for my kids, one for Christmas music, and an archive. They all feed into Plex automatically. Here is how I set it all up.

Why I still use iTunes

I buy used and new CDs, rip them in iTunes to ALAC, and keep my own lossless collection instead of relying only on streaming.

I also still sync music to iPods, which are honestly one of the most nostalgic and cost-effective ways to carry around a portable offline lossless library. For roughly $50 to $150, you can get a portable lossless media player with a lot of charm, compared to modern Sony Walkmans that usually start much higher. The new players obviously have extra features, but if you mainly want offline music playback, old iPods are still hard to beat.

When I am not using an iPod, I use Plex to stream my music to my devices.

So for me, iTunes is doing three important jobs:

• automatically ripping CDs to ALAC
• organizing files into a clean Artist/Album/ folder structure automatically
• syncing music to iPods

Plex then complements that perfectly because it expects exactly that same Artist/Album/ folder structure. So iTunes organizes the files, and Plex just picks them up with no extra work. You never have to manually sort or rename anything.

My hardware setup

This is what I use:

• a recertified Western Digital 8TB WD My Book that I bought on eBay for about $150
• an LG WP50NB40 slim external Blu-ray drive from eBay that the seller had already firmware-flashed so it can also rip 4K Blu-rays

The 8TB drive is just a very cost-effective way to keep a large media collection attached to my Windows PC.

The Blu-ray drive was just under $200, which is more than you need if you only want to rip CDs. I bought that specific drive because I also wanted to back up my 4K Blu-ray collection since discs can get scratched over time. If you only care about CDs, you can absolutely go cheaper.

How I organize my iTunes libraries

All of my iTunes libraries live under:

E:\Media\iTunes Libraries

I do not keep one giant library for everything. I separate them out.

Right now I have libraries for:

• me
• my wife
• my kids
• Christmas music
• an archive library

That setup solves a few problems really well:

• my wife does not have to dig through all of my music
• explicit music stays out of my kids' libraries
• I can keep special-purpose libraries separate instead of dumping everything into one giant mess
• Plex works nicely because I can point each Plex account at the correct music folders and keep everything isolated

The archive library is especially useful when I buy a big pile of cheap CDs. I can dump everything into the archive first, then later move only the albums or tracks I actually want into my main library.

How to create a new library

To create a new iTunes library on Windows:

1. Hold Shift while launching iTunes.
2. Click Create Library.
3. Put the new library under E:\Media\iTunes Libraries using the name you want.

Once the library is open, I immediately set a few preferences.

Go to:

Edit -> Preferences

Under General:

• set When you insert a CD to Import CD and Eject
• click Import Settings
  • set Import Using to Apple Lossless Encoder

Under Advanced:

• enable Keep iTunes Media folder organized
• enable Copy files to iTunes Media folder when adding to library

With that setup, the workflow becomes very simple. Open the library you want, put in a CD, iTunes imports it automatically, ejects it when done, and keeps the files organized correctly under that library.

That is one of the main reasons I still like iTunes. It is old, but for this specific job it is extremely straightforward.

How Plex fits into this

Plex works really nicely with this approach.

Because each family member has a separate iTunes library and separate music folders, I can create separate Plex accounts for myself, my wife, and my kids, then point each Plex music library at the right folders.

That keeps everything clean and isolated without having to manually babysit playlists or metadata hacks just to keep family members separated.

The main frustration with iTunes

A small source of frustration with this whole setup is library switching.

Apple's only supported method is still:

1. Close iTunes.
2. Hold Shift while opening it.
3. Keep retrying if the Shift key did not register properly.
4. Wait for the dialog.
5. Click Select Library.
6. Browse to the correct .itl file.
7. Open it.

That is annoying enough for me, but it is especially annoying when I want my wife or kids to have an easy time opening the right library before ripping a CD or syncing music.

I also found that making a shortcut directly to an .itl file does not solve this. iTunes does not respect which library you are trying to open that way. It will just reopen whichever library was last used unless you go through the Shift-launch method every single time.

The tool I made to fix that

Because of that annoyance, I spent hours reverse-engineering how iTunes handles library switching on Windows and built a small one-click Windows app to streamline it.

The app lets you:

• add all of your iTunes libraries to a list
• create new libraries directly from the app
• single-click to open whichever library you want
• create desktop shortcuts for each library so you do not even need to open the app itself

So now my real workflow is much simpler:

1. Double-click the shortcut to open the library I want.
2. Insert the CD.
3. iTunes imports it automatically.
4. The album ends up in the correct library.
5. It is ready for Plex, iPods, or both.

If you want to streamline this same kind of setup for yourself, or just want to buy me a coffee for the investigation and the tool, I put it here:

https://ko-fi.com/s/203812a2b6

Why I recommend this setup

I recommend this overall setup for anyone who wants:

• a straightforward Windows workflow for ripping CDs to lossless audio
• a self-owned music collection instead of relying entirely on streaming
• separate libraries for different family members or music categories
• easy syncing to iPods
• Plex integration for home streaming

If anyone else here is still using iTunes this way, I would be curious to hear what your setup looks like.