I still use my click wheel ipod. The UI makes finding my songs much quicker than on my phone, and it can create on-the-go playlists just by holding down the button, which Apple still hasn't figured out how to do on their phones. And finally it has a high quality DAC so music sounds better than from my phone.
Yes ! the clickwheel is too good, it has no competition in the UX dept be it with the Apple OS or the Custom aftermarket Firmware.
Still rocking a 5.5G iPod 30GB, Recently modded it with a 200GB MicroSD and it runs on the Rockbox which is Open Source and doesn't have any limit on the songs or storage that my other iPod Classc 6G 80GB has, thanks to Apple for that limit on the 6G iPod Classics, Rockbox can break that limit, But yeah you always need to boot to OF (Official Firmware) to copy tracks onto the iPod else there will be song skipping etc, Perhaps due to the third party HW chipset in between which is the SD Adapter (this is for every iPod 5G-7G with aftermarket modded HW)
And also yeah the 5.5G iPod (I think there are older iPods with this chip plus the iPhone 2G also had this/the same company's chip and 1st gen iPod Touch as well iirc) DAC chip is from Wolfson Audio which used to be great before the CL (Cirrus Logic) engulfed them & this makes it great fun to listen over my CL chip 6G, forget the phones, Apart from the Wolfson powered Voodoo modded Android phones nothing comes close to that level of detail, fun.
To people who want to mod them head over to the iFlash and get a hold of it, you'll be shocked to see how robust these things are. Plus there can be lot of inter mods that can be done like you can fit a 5.xG chipset into a 6-7G shell and vice versa - the frame can be interchanged+faceplate also goes in hand with the respective frame or need to shave a few bits off the metal frame, along with the backplate, headphone jack/hold switch flex cable plus massive battery upgrade(s) also exists - 2000mAh and up, these all are interchangeable. The Clickwheels, LCD panel aren't)
I've been thinking about replacing the hard drive and battery in mine for the past few years. The wheel-based iPods really did have the best UI for music in any device I've ever owned. If you're familiar with it, you can navigate with extraordinary ease.
Years ago, I replaced the 20GB drive in mine with a 30GB drive, because I was having issues. It was pretty easy with my 4th-gen iPod. Turns out that the issues were actually in the USB interface, not the drive itself. So I struggled to get the drive re-filled, and haven't changed the data on it in...probably 7 or 8 years.