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In the same vein as the PowerPC Mac thread, here I am again with the iPod thread. They're a lot of fun and still have a place today (I've yet to see anything better at Just Doing Music than an old iPod).
Why?
Playing music on a phone fucking sucks. It inherently encourages you to do other shit instead of paying attention to your music, and your phone feels completely happy to just duck your audio out to beep at you or ring whenever it feels like. Add to this the fact that most people are streaming music now, not only are you being told what to listen to by some faceless corporation, the device you're listening on gets to decide whether you're interrupted or not. Stop letting your phone be the boss of you and put your music back in your own hands.
Additionally, given how little artists get for streaming plays, you're better off buying on bandcamp for small artists and pirating the rest.
What?
There are a number of maintainable iPods - basically all the ones that originally came with hard drives. For most of what you'll want to do with them you'll only need a #00 screwdriver and a pry tool or two. Most of these are pretty easy to obtain but there's a few that are a bit of a chew to deal with, so a quick bit about all of them:
1st and 2nd Generation:
These are pretty cool but usually sell for absurd prices cause of scalpers and "I know what I have!" types. They're also an absolute chew to deal with - you have to have a FireWire port to sync, won't take flash upgrades at all (you lose FireWire, so, any way of talking to the iPod), and have very small storage (5GB for the first generation!) that's difficult to upgrade (you can only swap single-platter drives between 1st, 2nd, and 3rd gens so maximum you'll get is 30GB). The screens are also quite poor (whether from age or just early LCD tech) and they're not compatible with all the fancy iPod dock ecosystem junk.
The first generation has a real wheel that spins, while the second is a solid-state laptop-trackpad type thing. You can tell these apart mostly by the amount of recessing on the wheel and the firewire port flap thing on the second gen:
3rd Generation
By far the coolest looking iPod they ever made with the wackiest control scheme - all the buttons are capacitive and touch sensitive, so they're pretty durable, and it has some badass backlighting. Unfortunately it's also a chew, but less so than the first and second generations - this one only requires FireWire to charge. This means you'll need a FireWire cable + port on computer or wall wart. However, this often means people are selling them at bargain prices cause they think they don't work after plugging them into USB. Can be flash-modded but is extremely picky about what it wants to work with, and you lose FireWire syncing. Some people have made cables that hook the FireWire charge cables up to USB power delivery. You have options, but it's largely not easy.
iPod mini
Screeching swerve to briefly discuss the most popular iPod of 2004-5. Originally gimped by their tiny 4-6GB storage, these little guys have a new lease of life now, as one of the cheapest to buy and easiest iPods to expand storage on and own. Works like a treat over USB no problem, and you can swap the tiny microdrive out for a compact flash card or CF to SD adapter without much trouble at all. Only caveat is these have such a small screen that they don't display the album name on the now playing screen. There are two generations of these - you can tell from the text colour on the clickwheel and the label on the back. First gen minis can see up to 128GB, second gen up to 256GB.
Fourth Generation (Mono + Color)
The classic white iPod. Does come in two variants, the older monochrome variant and the newer version with a color screen. No syncing problems (none of that past this point), and will happily flashmod up to 256GB with a couple of cheapo adapters. Replacement parts are fairly widely available for these models, so if you get a beat up one you're probably not in too much trouble. The color display variants are slightly thicker. Both are great options, and as a small bonus the color display one can display album artwork. Both of these models go for fairly cheap still for some reason.
5th Generation (video)
We're now getting into the realm of "enthusiast" iPods. Originally available from Apple in black or white, these guys were the first to play video and have a much larger and improved screen to match, though there are better options for that now (I'll admit I've been watching King of the Hill on mine though). What makes them cool is that there are loads of aftermarket parts floating around for them - you can get various different color faceplates, clickwheels and back panels (or even brand new ones in the original colors). You can do big battery mods on these with a thicker back panel, and flashmod up to 1TB without things getting too fucked up. Word of warning, the aftermarket faceplates are more scratch prone cause they use poorer quality plastic (thanks China).
6th Generation (iPod classic)
By far Peak iPod, these were the last proper iPod Apple ever put out, and are available in a few iterations. If you're looking to flash mod with a large capacity, you'll want to look for the thin-backed 160GB second revision from 2009-2014, as the others use a weird addressing scheme and can't see more than 128GB of storage. Avoid the thick-backed first revision 160GB model as it's a hacky mess inside. These guys have the same availability of aftermarket parts, including colored faceplates etc. - I've actually swapped all the case parts on mine as they're quite often dinged up coming from eBay.
Word of warning: These are such a fucking asshole to open it's unreal. You have to work extremely thin implements in and manually unlatch at least six clips rather than prying. I watched so many videos and nothing could prepare me for how much of a trauma this was. If you go ahead with this, for fuck's sake please buy a chainmail glove, because you WILL cut your hands trying to get in. Don't buy one of these in nice condition, cause you will ding it up trying to enter - and you will have to enter, as these guyses batteries love to swell. Just get a nasty looking one and replace all the case parts after you fuck 'em up getting them apart.
Other iPods (nano, shuffle, touch)
Avoid these. They're fucking brutal to open and you can't upgrade the storage. Later iPod touches have okay storage but they're basically just phones so you're back at square one.
How?
The good news - these still work just as well as they did in the 2000s, and software support is still very much there. The latest version of iTunes for Windows, and the latest macOS support all iPods ever made assuming you can plug them into the computer.
You can get into most iPods (except the 6th gen as mentioned above) with a cheap metal pry tool and you'll need at most a #00 Philips screwdriver (5th-6th gen, iPod mini) or a Torx T5 screwdriver (1st-4th gen). The rest is ZIF connectors and plugs that can be taken apart by hand.
Flashmods are easy on iPods that like them - you can either get fancy ones from iFlash (iflash.xyz) that are slightly more expensive but always work (iFlash Solo or Quad for 5-6th, iFlash ATA for 3rd-4th), or a cheap green ATA to CF (3,4) or ZIF to CF (5,6) board and a CF to SD adapter. iPod mini is the easiest by far in that you can just get a CompactFlash card (though a CF to SD adapter works too).
If you've been into streaming for a while you might wonder where to get music - I mostly buy/download from Bandcamp or use ytmdl to yoink music off YouTube with tags at 320kbps mp3. There is something therapeutic and fun about curating your own music library instead of just letting some algo do it for you, I highly recommend it.
What else?
There are more advanced mods you can do as well. One of the ones I do fairly often is swapping out the iPod's piezoelectric clicker for a taptic engine from an iPhone 7/7+ - this turns the annoying click noise into haptic feedback which is super nice, but you need a soldering iron and fine tips to work in the cramped spaces involved.
In a similar vein of requiring a soldering iron, you can sneak a bluetooth transmitter in and hijack the iPod's power and headphone jack output so you can use them with wireless headphones - I haven't done this yet but it does seem like fun.
Additionally there are a bunch of wacky accessories to look through from the peak of the iPod's popularity, speaker docks, FM transmitters, breathalyzers (yes) and, uh, vibrators.
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