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Digitise My Life.
Bear with me on this one. I'm asking for advice but I think it could be a useful reference topic.

I am a hoary old dinosaur when it comes to entertainment media. Not only to I get music CDs, I actually pay money for them. How appalling. So I have ended up with several hundred CDs, a few hundred books, and some games.

Now I want to strip down my physical possessions and start transferring some of this to digital storage (and keep purchasing that in the future).

Thus I would like some advice on the matter:

Books: Kindle - seems to be surprisingly functional, but with a small screen. Is it limited to the small screen size? Is it easy to get all sorts of books for it? What is the overall experience like?
(Bal this might be one for you)

Music: Iwotever - as much as I loathe the idea of giving Apple a single penny towards their pompous fashion-driven bollox, I am assuming that I-blah is the best portable digital music option. I had a look, the new Nano seems to be pretty cool. What sort of options are there for storing music on these? Are the lossless / high quality formats worthwhile? I'm used to CD quality in general.
What are the options for listening in a car with only a normal CD player? Again quality is an issue.
How easy would it be to transfer a fuckton of CDs? Are non-mainstream albums generally available for release?
(Friction this might be one for you)

Games: I assume Steam is fine for everything these days??

Cheers,
Sham x
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One Hoary Older Dino To Another... 
I also didn't want to go the iTunes route and I had around 250 LPs as well as a similar number of CDs to worry about. I used the built-in Window media player that was with XP (at the time) and used that to copy all of the CDs over a couple of weeks. It looks up album art automatically and I have never had any issues with it.

The LPs were a differnt story so I purchased some software and spent the best part of two years moving them to the HD. I also have an iPod but still use the Windows media player to do all the transfers - again, I bought some software to assist.

If your car CD player is not too old, you can just copy mp3 tracks to a writable CD (assuming that you have a CD writer in your PC) and play as normal. If you have an aux socket on your car stereo, you should also be able to connect any mp3 player by using the player's headphone socket with a cable suitable for your car's aux socket. If you are driving around in a fairly new (flash) car, you may already have iPod connections built in.

I have a number of portable mp3 players, and even though I am not an Apple fan, the iPod is pretty good at what it does. I have over 10,000 tracks, with album art for everything, and still have plenty of space left for more.

However, I also have my music backed up: one copy on the desktop, one copy on the iPod, one copy on the laptop, and a final copy on a backup HD (along with other data that I need to back up e.g. all my Quake maps and stuff) outside of the PC. Again, I use bought software to organise the backups.

I am now in the process of cataloguing my LPs ready to try an eBay sale.

Bit of a ramble, sorry about that. 
 
Kindle locks you in to buying books from Amazon -- usually they'll have pretty good deals but it's still a very unwelcome limitation and considering Amazon's questionable business practices (for instance, they've engineered their finances so that they don't have to pay any business tax in the UK, effectively allowing them to trample any competition) I'd advise either getting a Sony e-reader or a tablet which is much more versatile and could also solve your music dilema if you choose the right one.

iPods are well-made hardware but sadly Apple are as closed minded as Amazon when it comes to limiting their customers' choices to their own advantage. It would also require installing iTunes, which is the worst software in the world. Most Android smartphones can be used as a decent enough MP3 player if you install the right apps. 
Oh, And Another Thing... 
You can buy an FM device that takes a feed from the portable mp3 player, passes it through a small FM transmitter, which you then pick up on your car radio just like any other FM radio station - your mp3 player is effectively the radio station albeit that it happens to be inside your car.

The downside to that is finding a suitable FM frequency that is far enough away from other, more powerful transmissions, is not always easy. Also, as you travel around, you can move in and out of the range of stronger signals, which buggers up your mp3 player's signal. I found that it worked OK locally but when going on longer journies, I would have to regularly change frequencies to keep a clear signal. My particular FM player has 6 presets, which I have also programmed into the car radio, so it is not too bad.

That all probably sounds far more complicated than it really is. 
Shambler 
Nothing wrong with mp3s. MP4 is just mp3 with apple's arsehole attached. You can back your media up onto....


...computers!!!

People have been doing it for years.

</sarcasm> 
I Would Rather Stay Dinosaur 
i'm still one of those guy's who want cd's and dvd's of their games/music/movies.
Nothing wrong with it. 
 
i gotta go convert all my vhs cassettes... 
Er... 
...should I convert my penis to an usb plug? 
If Quality Is An Issue, 
avoid mp3 at all costs! That said, I own Macs since more than 20 years. and my current iPod is a 4 yo 80gigs classic. Both iTunz on my cpu and the pod are packed with 800 albums. 4 years ago I've re-encoded/dlded everything in mp3 320kbps and got rid of everything else. Mp3 is not the best lossy format, but it's universal. 320kbps for quality. Avoid anything below. Use/check for CBR (constant bit rate)encodings. This is mandatory with gapless albums: the apple soap system doesn't stitch VBR (variable BR) files so well. It often results in sound glitches between songs or worse, it just stops playing at the end of a song due to bit rate difference between songs. Lossless and iPod is a nono. Although it may seem to play OK, the buffer size of the pod is too small to store big aiff or wav files. The pod becomes very unstable and stutters or stops when shaken a tad. Very bad in as a choice for car audio! Regarding this problem, Apple lossless (aac) provides better sound than mp3 and smaller size as aiff/wav, but is proprietary. Needless to say you can't use flac or ape with an ipod.

En r�sum�, I love my pod and I use it a lot: backpacking, camping, always in a pocket, easy to hook on whatever sound system to save the party, cool with earphones� TEH easy going music solution. But� if you're picky with quality and/or used to listen music on good audio gear or PA system, these mp3 will sound like crap. I'll add here a huge thumbs down about anything you can buy on iTunz: low bit rate encodings (you can't even check what encoding is used b4 buying!!), still crippled with DRM� long story short: a very expensive pack of BS for herds!

I'm a lossless lover. Flac or Ape are the most common (free) formats. You can play them as is, although you'll get the best sound quality once expanded to wav or aiff. Lossless files can be burn to CD on the fly (true mirrors of originals!). I currently have some 2000 lossless albums, all nested on a 2TB HDD together with my iTunz library. I use a small nifty free player, loaded with all type of AU plugins to route the sound through various small and bigger sound systems in my house. Cpu as the hub. Remote control software + cellphone�
Now when it comes to my van, I just love a big fat quality sound to drive with. My advice, stick to CDs! Run some parallel tests with an ipod� The difference will blatantly jump to your ears! Now, CDs are so cheap, easy and fast to burn� My car is rigged wit a CD charger full of copies. Lossless files stay home with my precious original CDs collection. CD copies are so cool. They're expendable and duh� even sound as good as originals!

En r�sum� de r�sum�: If the main criteria for you is smaller as possible, always at hand not so much nitpick about sound quality: go for a pod.
If sound quality is above all the deal for you but you're still concerned (a bit) about HDD space (even nowadays?), go for lossless or audio CDs.
And why not going for both?

Last word, iTunz is a big fat bulky mall for the masses. Still a necessary evil companion of a pod (3rd party pod managers are cool and required if you once want to transfer songs from your pod to someone else's cpu (iTunz doesn't allow that!!). The less you use it, the less you *upgrade* it, the better. Find a compatible iTunz version for your pod, then stick to it! ITunz behavior is for sure the most user-unfriendly I ever met on the Mac. Go figure! 
 
This is mandatory with gapless albums: the apple soap system doesn't stitch VBR (variable BR) files so well.
Thanks for this, I always wondered why it did this. :S
Gonna take ages to rerip everything. :\ 
 
if you want quality, use ogg vorbis. I am not saying that as lunix lunatic but because it is a fact that vorbis sounds better than mp3 at similar bitrate.

if you plan to transcode, use flac. if you must use mp3, use v0 or whatever you can hear (abx test).

if you think you can hear the difference between a good encoded vorbis or mp3 and the lossless source, make an abx test.

johnxmas does not seem to know anything if he suggests that a wav sounds different from a flac. lossless means lossless.

if you must have a ipod (god, why), put rockbox on it. otherwise I can recommend the sansa clip+ (with rockbox of course). it is tiny, light, cheap, you can stick SD cards into it, works as normal usb storage. I got 36gb in mine.

I would not rip myself but just download rips from somewhere to save time and ,energy.

I hear Amazon sells good music too.

those fm transmitters might suck and not work, depending on what you (uk regulations etc) 
Ps 
rockbox plays gapless without problems. cbr is either a waste of space (at high bitrates) or a waste of quality (at low bitrates).

http://www.rockbox.org/ 
 
Spirit, Playing Lossless File 
straight from it's format results in degraded audio. OK. maybe *degraded* is a huge word here, since not many human ears will notice the difference. But there it is: lossless format is compressed anyway: a regular lossless audio CD is some 1/3 smaller than the the original wav/aiff CD. Thus, when playing a CD straight from it's lossless compressed file form, the audio is decompressed on the fly. Which results is audio losses. These are quite neglectable, listening wise, nonetheless mesurable. And probably with various results depending on the software/player/gear. But, outside of this yes, lossless reveals it's full losslessiness (!) only when uncompressed in aiff/wav CD format.

Btw, other brands of walkpods or software may be able to play gapless VBR, however, this has always caused problems on iPods, afaik. Maybe recent models circumvent this. Necros, which gen model do you own? 
Ogg Vorbis, 
as a lossy format choice, sounds better as mp3 at similar bitrate yes. Moreover, it's a free codec. On the other hand, like flac, vorbis, is not as widely compatible as mp3. Another thing, doing my tests I remember having run into problems with Ogg Vorbis CBR, maybe corrected now.
Anyway, we're talking about some megs in a lossy audio world here, No big deal, if this can prevent any uncomfy listening moments... 
Let's Be Serious 
If Shambler wants to listen to music in his car, the quality of the recording is hardly likely to be an issue is it? Try engine noise, wind noise, tyre noise; his six kids in the back arguing about life, the universe and the merits of stealth versus all guns blazing in sixteen year old computer games. 
Bler 
As you know i'm the same in terms of music fanatism, having 930CDs in my collection I got tired of looking for certain CD in those vast shelves just to listen to it. So i took http://legroom.net/software/autoflac and decoded ALL 900 CDs to flacs. This is lossless format, everything plays perfectly. I'm now converting my vinyls to flac too, so i play them less and save their lifes.

Just read that autoflac page for instructions, but basically all you need is Exact Audio Copy program and this autoflac script, it'll do everything for you.

ps. books - kindle, games - steam, no other options. 
Oh And 
to play all those 300Gbs of flacs I use excellent player http://www.foobar2000.org/. it's light, easy to costomise and has no flaws at all.

ps. to convert all those 900CDs to flacs took 3 months of lazy copying and not every evening. 
Ah Ah, Good One Mike! 
but even with a bunch of shrieking vores playing ball on the backseat you'll instantly notice the difference between a CD and a pod-player (in hi and low-ends mostly, but overall clarity too) whatever the car audio system quality...

On the software side, whish we had Foobar2000 for Mac! Great app! The current sleek one for OS X is Vox. Not as sharpely refined as Foobar though... 
Kindle 
What Text_Fish says isn't true, you can buy from wherever you want with the Kindle, not only Amazon.
The screen isn't too small, it's quite perfect, and the device is really light and easy to carry around, I read it standing up in the subway, or even when waiting in line at stores or such.
Now that I have it I just want to get rid of my 200+ paper book collection.
Books are really easy to find, I haven't had any trouble finding anything I wanted to read (from amazon and other sources), and it's nice to not have to buy hardcover books for new stuff you'd want to read as soon as possible.

The other e-readers around are probably good as well though, but I haven't tried any of them.
I wouldn't suggest a tablet if all you want to do is read, it's more expensive, heavier, and the screens aren't as nice as e-ink. 
Kindle 
Yes, fully recommend one as well.

I haven't bought a single book from Amazon on it, and more than half the books I have are public domain - ie. free, downloaded from websites legally.

Don't bother with the fire, you want the eInk version, though if you want to read pdf then go for the touch version. The keyboard is fiddly and goes unused.

The free Wi-Fi sounds good, but I've never turned it on since it makes the battery drain quicker and have no use for it.

Finally, use Calibre for it - which is like iTunes but not a completely shitty waste of time.

Which brings me to portable music - fuck iPods. The machine itself is quite nice but the software is the worst I've seen since Windows Vista.

Why not just spend the money on a slightly nicer phone? 
And 
Steam is great. 
Forgot The Link 
Foobar 
I'll throw my recommendation out there for Foobar2000 as well. Been using it for years! Fantastic no-fluff music player. 
 
Johnxmas: you are falling victim to confirmation bias. lossless means lossless. think of flac like zip or rar. what you compress loses no quality.

show me some research, test results, measurements.

-----
willem, sorry to hear that. 
 
and the screens aren't as nice as e-ink.
That's the big appeal for me. It's like reading from paper, very easy on the eyes. 
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