(All prices I mention include shipping.)
I upgraded my stock 30GB 5.5G iPod to 240GB with a new, higher capacity (850mAh, stock is 590mAh) battery, new Rockbox firmware (I dig that there's a iPod Video UI theme) and the transparent iVue case all at the same time this last week. It's about as difficult as you can get modifying electronics using just three simple tools and no soldering. The hard drive you want is a Toshiba MK2431GAH. You can buy the hard drive itself from China for around $130 USD. For about ten dollars more you can get it in a kit with all the bits and pieces you'll need to upgrade, a battery, and opening tools. I think it's worth it, generally if you're opening your iPod for the first time you want to put in a new battery upgrade, and although I was being frugal I didn't mind paying an extra handful of dollars to make sure I had all the internal little plastic pieces and cables I needed. I didn't want to be in the middle of installing my HDD and find that I needed a $0.02 plastic piece or hard drive connector that I was missing and needed to order from China, delaying me for a month. Since I had a 30GB I also needed a thicker back and the plastic piece that hugs the dual-platter hard drive. I payed $150 for a 240GB upgrade kit from an eBay seller with good feedback that included a new customized iPod back (with a new headphone port) that has "240GB" printed on it (otherwise it's just like a standard new iPod Video back). I then spent another $15 to buy my new iVue case and a plastic screen protector from Rapid Repair on eBay (less expensive than on their own site).
For $250-$300 (depending on your options) you can get it professionally installed in the USA by Rapid Repair. For most people, I'd say it's worth the peace of mind. The company has a fine reputation, you can get a warranty, and rest assured your parts will all be legitimate. Personally, with my $300 upgrade budget I decided to take a risk and spend $150 on a kit from a no-name in China with no warranty instead of $300 with Rapid Repair, and I took the $150 I saved and I'm going to spend it on a Teclast T51 (Nationite S:flo2), to complement my "best high-capacity digital audio player" with the "best sound quality digital audio player" (well, short of paying a hefty sum for a HiFiMAN HM-801. The sound quality on the T51 from what I hear is comparable to the iMod (at a third of the price of modifying my iPod). I was about to buy the Teclast T51, but with Teclast's new line of X19HD, X29, and T59 in production, I've decided to wait a few months for the reviews and impressions here on Head Fi rather than live with an obsolete player. kiteki was an evangelist of the X19HD which has recently been released, but I haven't seen his impressions posted yet. I've so far only seen brief comments from one person, who say it's good but did not compare it to the T51. I'm not necessarily expecting Teclast to match (let alone exceed) the T51's sound quality in their new products. I hope they will, that's why I haven't ordered my T51 yet.
I recommend professional installation if you're not technically capable and very careful and you have a job in a first-world country. Many people aren't careful enough when opening their iPods for the first time and damage some component. I saw a lot of messed-up cases and cracked screens on YouTube. The part of the process most likely to cause damage is the first step of opening the iPod for the first time. (Removing the plastic from the touch wheel and replacing it with plastic for my iVue case was by far the longest, most difficult, taxing, and tedious part of my upgrade and was the part most likely to cause damage even for careful installers.) Now that I have the experience of upgrading my iPod, I can open my iPod quickly and replace any component easily. The only part that remains difficult is closing the iPod: the battery cable connection could not be in a less user-friendly position, making connecting the battery and closing the iPod very difficult. You have to close the case almost all the way just to give yourself enough length of the cable, and then, with barely enough room to hold the cable with a finger or tool, connect the cable and lock the clip.
Alright, I've given you a lot of information, some of which you may not need, but this should be important for you: I can confirm that a 240GB RWA iMod iPod is possible, because the 240GB hard drive is exactly the same size as the 60GB and 80GB iPod hard drives. All the 1.8" dual-platter iPod-compatible hard drives are the same size (all the single-platter drives are the same size, too).
I've fantasized about having an iMod myself: I think few would argue with my assessment that an iMod 5.5G iPod (or similar Whipmod and DIYmods) with the highest capacity drives (240GB MK2431GAH, and I think similar capacity SSD drives have been successfully installed) is overall (we all have different desires and needs) the best commercially available digital audio player in the world right now- or more specifically, the one that excels in the most ways. You can't top it in any way without extreme compromises (which depending on your needs can be justified). It's the HM-801 might have slightly better sound (significantly better sound with 96kHz/24bit audio, which no other DAP can play, although few us listen primarily to high-res audio), but it has far inferior UI (iPod has the best UI options in the business: the iPod stock UI is very good, and Rockbox is excellent and FLAC compatible) and the capacity is dwarfed by what the iPod offers. Size and weight wise, it's comparable to carrying a portable amp strapped to an iMod. Plus you'll need to carry a case of SD cards if you want more capacity. That said, if you don't need to carry a large collection of music, you listen to high-resolution audio, and good UI isn't important to you, I would definitely recommend the HM-801 over the iMod. The only thing that tops a modified iPod in capacity by a wide margin is a big clunky 500GB Archos tablet but it's a very poor DAP in every other respect. Of course if you're going for a run, you should compromise and use a Sansa Clip+ or Teclast X19 HD or similar decent small player. If you're not being still in a quiet space, it becomes much harder to notice the difference better sound quality. If I had $450 to spend to upgrade my DAP at this moment, I would immediately send my 240GB Rockboxed 5.5G iPod to Red Wine Audio to make it an iMod. It's the only way for me to carry all of my music in my jacket and then sit down and listen to it with CD-resolution sound quality the equal of any other player. The only other option for that would be the HM-801, which would mean alphabetically organizing my music collection on a dozen MicroSD cards and dealing with an inferior user interface.
I don't think RWA would have any problems making an iMod of an iPod that's already upgraded, but you may want to check in with RWA and whoever will be installing your new drive (if you're not doing it yourself) to make sure you won't run into trouble installing your new drive. There's almost no empty space in an iPod, and you'll have to work around the iMod. Unlike with upgrading a stock player, there aren't any guides with pictures or video for that on the internet, so you would be venturing into unknown territory. It's possible that professionals like Rapid Repair might have experience working on iMods before.
If you plan to make then upgrade yourself, here are the two upgrade guides (out of at least a dozen I read) that I found most helpful:
Detailed step-by-step guide with photos (includes important details I didn't find anywhere else in days of research) [computershopper.com]
Macworld's HD overview of the process on YouTube (includes important high-quality footage of how it's done)
And here is Rapid Repair's site.
I hope this post is helpful. As far as SSD goes, I honestly think it's a waste of money for most people. I used to exercise and run with my 5.5G 30GB iPod in a Contour Showcase case clipped to my waistband, and my hard drive still functioned well after five years of mostly regular use, up until a few days ago when I replaced it for 6x the capacity. I never should have had a 30GB in the first place, I hit the 30GB limit years ago and spent years micromanaging my iPod to work around the capacity limit (I'm a member of the lossless club). I'm not afraid of running with my iPod hard drive (although if I start running regularly again I'll buy a Sansa Clip+), and so I don't see a reason for anyone to spend hundreds of dollars on a SSD drive just for additional shock protection unless they're planning to expose their iPod to regular, hard-drive-killing extreme vibration. Just buy a good iPod case. You'll have money you can spend on improved headphones to measurably improve your listening experience, or have money around to replace a iPod component in case it ever fails. Even SSD drives fail. If you're looking for an iPod 5/5.5G case, I think the Contour Showcase is just about the perfect iPod case and the best ever made. But I can't find one to buy any more now that they're out of production (I need the larger size now). I bought a Griffin iClear Photo (iClear is almost the same) instead for $3.50, I'll see how it is.
Rockbox can play 96kHz/24bit FLAC files. I'm not sure if it downsamples it, though. I can't hear a difference off of my iPod, but I don't think the headphone out is good enough on an unmodified iPod for me to hear a difference. Hopefully the limitation isn't in Rockbox: I would be very interested to know if an iMod can output 96kHz/24bit FLAC well enough to take advantage of the superior fidelity.
While I'm at it, I might as well share this little-known nugget knowledge I learned while reading about Rockbox: the 30GB iPod 5/5.5G has 32MB of RAM, while the 60/80GB has 64MB of RAM. This is pretty much useless information for most users, but it's curious. Perhaps the extra RAM provides a very slight boost to battery life by reducing hard drive usage.
I would offer to upgrade your iPod myself for $100 (plus the cost of materials, so around $250 plus shipping) if it wasn't an iMod. I'm curious about the process of upgrading an iMod, but I have no experience working with one and I'm not willing to take chances with anyone else's equipment (especially if they're paying me).
Edit: I edited this post 30 hours after posting because I wanted to separate and clean up the section where I compared the iMod favorably to other players. I considered deleting this paragraph for perhaps unnecessary value judgements that I was worried might be a little hyperbolic, but after a little editing to make it tighter (but longer) I decided to leave it in because a comparison between the DAPs with the best audio quality available, the iMod/Whipmod/DIYmod and the HiFiMAN HM-801 could definitely help some people. Those are the only two players that are generally considered to best the cheaper Teclast T51's sound quality, and without having with it's awful UI that is a deal-breaker for many. Although I do believe that if you're listening in the subway, even with great headphones you'll be hard pressed to tell the three apart. Anyway, that was the only paragraph I modified.
Edited by Jonah - 11/30/11 at 4:08am