I have a lot of experience with almost all iPods and iPhones, so I want to share it by providing an updated guide. I will keep this simple and Stock OS/hardware-focused, and providing pros, cons, advices, and thoughts about each options.
I will focus on options that I personnally tested and experimented.
The last iPod models from the Clickwheel era.
Pros:
- The board is the most efficient regarding power management. It is much more efficient than older iPod and can get 30 hours from the stock sized battery.
- The Classics 6.5+ supports in-line controls from your headphones
- A lot of parts available to buy (battery mods, custom shells, multiple iFlash boards)
- Can support around 50 000 tracks before getting serious stability issues thanks to the most advanced Stock OS, which is much bigger amount than previous iPod models capabilities. Older iPods tends to have issues between 15000 to 30000 tracks depending from the size of the metadata.
- Can syncs music much faster than older iPod models (around 2x faster)
- These have the best color screens.
- Can play the Clickwheel Games with the best possible performance.
- Some cool gadget features: Genius, Cover Flow
Cons:
- The "On-the-go" playlist is annoying to build on device because it asks for a confirm each time you want to add new content to it
- iPod Classics 6G and 6.5G are limited to 128GB storage mods on Stock OS.
- More difficult to open compared to the iPod Video
Advices:
- Don't mod this kind of iPod with a green board + a CF card, there's annoying sound noises when there is disk accesses with this configuration. I recommend to get an iFlash Solo + an SD card instead.
- Check this video from Nekomichi to learn how to open as easy as possible this iPod: https://www.youtube.com/watch?v=a3gPf6obQHs
The model that introduced the final design, that Apple kept almost unchanged until the end of Clickwheel iPods.
Pros:
- A lot of parts available to buy (battery mods, custom shells, multiple iFlash boards)
- This iPod is the first model with a "big" screen that can show a lot of text from each lines. Also, the Stock OS is able to scroll in real time too long texts from the metadata of your songs.
- Can play all the Clickwheel Games with decent performance for most of them. A nice bonus to enjoy while enjoying the music.
Cons:
- Can't find any, it's a very balanced pod.
Advices:
- Get a 5.5G if you can, but 5G are fine. Don't feel worried too much about getting the 64MB RAM models, the difference is subtle with the 32MB of RAM models, and is noticeable only when storing more than 10K/20K songs.
- Don't mod this kind of iPod with a green board + a CF card, there's annoying sound noises when there is disk accesses with this configuration. I recommend to get an iFlash Solo + an SD card instead.
- Check this video from Nekomichi to learn how to open as easy as possible this iPod: https://www.youtube.com/watch?v=a3gPf6obQHs
A simple music player experience. For those who don't mind about album arts, photos, videos, and additional Clickwheel Games.
Pros:
- Minimalistic by design
- The mono screen is very readable even in direct sunlight
- Easy to open
- Navigation is insanely and impressively smooth even with tons of music and metadata. iPod Classics and iPod Videos are smooth enough in menus, but not that smooth and predictable, there's no such things as tiny lags here.
- Even when backlight is off, you can still often perceive clearly enough what's on the screen to check the progress bar. It is very convenient to show the progress of the current track/album when the iPod is docked. You lose this comfort when you switch to the modern iPods that have very unreadable screens when backlight is off.
Cons:
- Terrible battery life with Rockbox when flash-modded
- Can't charge through an USB wallplug (can charge only through firewire or when plugged on a PC because of an issue that was fixed only starting the iPod Video)
- Can't show album arts and long names in the menus. There's no text scrolling at all in these models on all menus. Scrolling happen only in the music playing screen. Though this model can show one more line and some more characters compared to an iPod Mini.
- Need a workaround to get gapless playback (play CDs without gap between tracks for CDs that were recorded to take advantage of gapless playback, like live performances)
Advices:
- If you CF mod it with a green board, you may get terrible noises during disk accesses, especially with the slim model. This can be largely reduced by putting a sheet of paper on the back case (when the iPod is opened) to provide some shielding. This was necessary to do on my Slim 4th gen, but my Fat 4th gen don't have no such noise at all.
- Putting together a slim 20GB 4th gen mono with a CF board can make the screen go off because there's too much pressure on the screen with this configuration so the screen basically stops working until you open your iPod again to release the pressure. It was difficult to put together. Now that I know this, if I have to build another, I would definitely use an iFlash-ATA1 instead.
- Get a FAT (40GB) 4th gen mono if you can, these are easier to mod and have plenty of available space. There's plenty of space there; so much that you can battery mod it if you want more and if you have some soldering skills.
Same as 4rd gen, minus USB charging/syncing. This model is known to have more issues when flash-modded. This model can also act weird with modern docks. Not recommended excepted if you know what you do.
The iPod Minis are the tiniest options regarding to moddable iPods. If you want the smallest pockettable device that can carry your whole library of CDs, it is the iPod that you want.
Pros:
- Minimalistic by design
- The mono screen is very readable even in direct sunlight
- Navigation is insanely and impressively smooth even with tons of music and metadata. iPod Classics and iPod Videos are smooth enough in menus, but not that smooth and predictable, there's no such things as tiny lags here.
- Even when backlight is off, you can still often perceive clearly enough what's on the screen to check the progress bar. It is very convenient to show the progress of the current track/album when the iPod is docked. You lose this comfort when you switch to the modern iPods that have very unreadable screens when backlight is off.
Cons:
- Not so easy to mod. Once opened, it's easy, but it's also easy to break something during the process which can break a complete logic board and requires soldering skills to fix.
- Terrible battery life with Rockbox when flash-modded
- Can't charge through an USB wallplug (can charge only through firewire or when plugged on a PC because of an issue that was fixed only starting the iPod Video)
- Can't show album arts and long names in the menus. There's no text scrolling at all in these models on all menus. Scrolling happen only in the music playing screen. The tiny screen of the mini can't show much text on each line.
- Need a workaround to get gapless playback (play CDs without gap between tracks for CDs that were recorded to take advantage of gapless playback, like live performances)
Advices:
- Avoid the 1st gen iPod Mini. Get a 2nd gen, there's an impressive difference between both models.
- You can mod it directly with an iFlash CF or any real Compact Flash card. The sketchy (but cheap) red CF adapter can work also very well for 128GB or less.
iPod Touchs have terrible repairability and no storage mods. You may want to get an old iPhone instead.
Advices:
- The iPod Touch 3G can be found in 64GB and can downgrade to any old iOS firmware which makes it a very interesting iPod to use on a legacy version of iOS.
- The iPod Touch 4G was running fast in iOS 5.1.1 or lower but it was ruined by iOS 6 because of it lack of RAM. It can't be downgraded untethered unfortunately.
- The iPod Touch 5G can be very interesting and run great for a music player between iOS 6 to 8.1.3. Unfortunately, it can't downgrade untethered and is very slow on the boring iOS 9 that is the last firmware that it can support.
- The iPod Touch 7G can be found in 256GB. With that storage, it can be even a good alternative to the Classics, especially if you really want Bluetooth. Bluetooth with an iPod Touch will be much more solid than any modded iPod Classic that don't have a dedicated UI for it.
- Check the prices. Don't put too much for a Touch, and do compares with old iPhones if you really want an iOS device, these are often around the same prices. Old iPhones have better repairability and some additional features like phone, GPS, and the brightness sensor to change automatically the brightness of the screen.
Terrible repairability, and no UI; very limited devices with very limited storage capacities.
iPod Nanos can be found for very cheap and can still be great daily-companions or gifts.
Pros:
- The small size
- Nanos 3G to 5G uses the most advanced Apple Stock OS with coverflow and all
- Nano 6G (the tiny one) is the size of a Shuffle but with touch gestures and a real UI
- Nano 7G have integrated bluetooth with a real UI that looks like old iOS versions
Cons:
- Terrible repairability
- No storage mods
- Very limited storage (often). Priorize 8GB models at minimum to get some margin even if your music library is currently very small.
- Battery expands over time which push the screen thus breaking the device
- Almost all nanos that are in online listings are with their original battery, which are all very old at this point. You take a huge risk to get a tired battery on purchase.
Advices:
- Nanos 1G and 2G can use Rockbox
- If the black spot appears on screen, it is recommended to stop using and to never charge the device ever again. You can safely put it in a jar forever with other e-waste, though.
Old iPhones have much better repairability than old iPod Touches, and tends also to be cheaper options. This can be an interesting path for you if you care a lot about old iOS games, which are far better than the iPod clickwheel games. Around 2010, the iPod Touch especially was a very popular game console. A lot of games were developed.
Maximum: 64GB Battery life for music: around 30 hours
Pros:
- Many old games can be sideloaded
- iOS 5 to 8.1.3 music app is great
- Great battery life for music
- A beautiful screen to watch videos on. It can even connect on YouTube with TubeRepair.
- Supports in-line controls from headphones
- Bluetooth
Cons:
- Storage is not extendable
- There's some DRM related to the battery. If you put a 3rd party battery, you can't restore that phone anymore excepted in pwnedDFU with Legacy iOS Kit.
- The jack port connectivity is flawed with some headphones that don't like it (same issue with the iPhone 5), like my Sonys. The connector seems to be more sensitive to movement/disconnections compared to the connectors used on old Clickwheel iPods.
Advices:
- Jailbreak it. Use Legacy iOS Kit.
- Use it below iOS 8.4 so you can to take advantage of the pre-Apple Music app. Avoid iOS 8.2 and iOS 8.3 too, there's issues with sorting here on the Music app.
The touch-based music app is very ergonomic and fast to use even when navigating through a lot of music.
The iPhone 5 can't be downgraded untethered to iOS 6, but it's the best device that can run it with a glorious 4 inch display.
Compared to the iPhone 4S, the iPhone 5 don't have any hardware DRM related to 3rd party batteries.
- Play your music wired. Wired headphones/IEM are always cheaper for better reliability/sound quality. Most wireless headphones are future e-waste because batteries can't be replaced.
- Avoid Bluetooth mods with iPod Classics. These are outside the spirit of the product and will add friction and issues.
- If you wanna use Rockbox, always use the latest daily build, don't use the 3.15 version. It will avoid you many issues.
- Use the yuuiko document to learn how to identify iPods and to know all the modding options for each of them: https://yuuiko.github.io/iPodGuide/iPodGuidev2-1.pdf
- The "Album artist" tag is completely ignored (excepted on iOS devices). Use Rockbox or re-tag your songs to use the composer field as the "album artist" one with a tool like mp3tag so you can get a decent view of your songs.
- You can get access for free to all of my guides on GitHub to take more advantage of your device: https://github.com/Olsro/reddit-ipod-guides
- Equalizers are bad on Stock OS, you should not use any
- Use iTunes 12.0.1 or 10.7 to get a stable syncing experience, if you can
- Get yourself an iPod Universal Dock or a Dock Speaker/Alarm Clock so you can put your iPod on it when you go back at home and it will play your music while charging it conveniently.
- Get yourself an iSesamo and common repair tools. Working with the best tools will reduce your risk of errors and the risk of making cosmetical damages on your precious devices.
- Stripping embedded cover arts or resizing cover arts (to 500x500 max jpeg) is very important and can make you save some GigaBytes easily if your library is huge. It's really something important to include in your music management process.
- Always keep your original FLACS so you can always change your lossy format later and even build multiple lossy librairies for different devices
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Thanks for reading !