CD ripping for the lower end.

n80,

I have ripped pretty much everything in iTunes and it works, but it is not as great as it could be when it comes to metadata. On the other hand, I am quite obsessive about that so it may not be of any problem for you.

After years of doing everything (ripping-wise) through iTunes, I bought dB-Poweramp and am happy I did. For $80, it does whatever I need and then some. And it does not ask me if I want to update it every time I open it. dB-Poweramp is a breeze when converting files from whatever to whatever, except for DSD. I know nothing about free software, but this works great.

In your case, first rip everything as AIFF. Along the way, make sure to copy files on a separate hard drive or two. You can put metadata in iTunes or in (in my case) dB-Poweramp. Most of the time, it will find it for you but sometimes it is not that correct. I am not sure about iTunes, but dB-Poweramp can look it up online for you. Results may be iffy, but if you are not too picky...

I am not sure what the problem with iTunes embedding the cover art in the file may be, but I have never lost it during conversion.

Once you have everything on that separate hard drive, convert it FLACs, Apple Losless, whatever you like, and store it separately. Then you can play all you want. As many times as you want. dB-Poweramp does preserve all the data, including cover pictures, as far as I could see. No need to think too hard about it.

I would suggest you keep AIFF on your computer and use it for that DAC, stationary system, and loading your iPhone.

If your portability includes a car, especially anything relatively new, you may want to remember where you put that FLAC hard drive. Most of the cars I have tried do not play AIFF from the attached storage device. They will all play it from a connected iPhone, though. At the same time, it seems that FLAC became an accepted standard. I tried plain 16/44.1 FLACS and 24/192 and it always worked. Your car may vary, of course but this is the general direction things may be going these days. You can load all 150 CDs on an SD card/jump drive, stick it in the car, and never think about what song you have on your iPhone or not.

In summary, I have iTunes with AIFF that I use only for loading my SONY server (that will switch to FLAC soon). I have dB-Poweramp to convert almost (not DSD) all I have to FLAC. I have all of that in FLAC that I use for loading Walkman (digital one), and that I have put in cars.

When comparing AIFF and FLAC at home, I have never found any difference. Cars do quite well with MP3, if you want to save even more space. In fact, I have a feeling they are tuned for that.

@n80

I agree with plan to use iTunes with BitPerfect to start.  That is what I do and the SQ is quite good.  The SQ with and without BitPerfect is large and instantly noticeable.  I think BitPerfect probably largely ameliorates the negative reputation of iTunes, although I should bite the bullet and try out the others.

I also second the suggestion to try a MultiBit Schiit DAC, the step up from the Uber level was the first time I thought digital sounded like music.

Get dBpoweramp and rip to flac. With xld it’s very hard too have any control over folders and sleeves. I have used both, and also Pono. dBpoweramp is best. 

One of the main challenges to overcome with digital playback is noise (many types including electrical, RFI, EMI, etc.) coming from the digital player (i.e. computer or network steamer/player). This is especially an issue with older devices outputting the digital music to the dac via USB. In the last couple of years manufacturers have greatly improved USB outputs in high end audio purpose built players. OTOH, macs & PCs have USB outputs not optimized for audio sound quality. That's why so many approaches have been utilized to attack the problem including: dual-headed USB cables that separate power from signal)
filter boxes that disengage the power leg of a single USB cable
decrapifiers
upgraded linear power supplies
low power linux players running few proceses

For all these reasons stepping up in SQ at reasonable cost for most of those in the know involves going from a full purpose computer running high power and an O/S running tons of processes that don't involve audio to a single purpose built low power player, regardless of whether the storage is local or in another room and connected via network(NAS).

When you make that change you'll probably change software too, although you might not. Whatever choices you make now should position you to make those changes without having to convert all your files or edit all your metadata. One example is that albumartist is a key metatag field in many software programs and often ripping won't populate it. Do yourself a huge favor and edit your metadata when you rip each disc and populate that field with artist name or soundtrack title or whatever else might be the thing you most want to look up your disc by. Cheers,
Spencer

Thanks guys, a lot of good info here.

One glitch in my plan: The Schiit Modi 2 Uber will not work with the OS on the old iMac according to Schiit's website. I'll try it but doubt that it will interface properly.

So, I may be using the MacBook anyway.

Glupson, you mention $80 for dB-PowerAmp but I see the single license for $39.

Finally, an admission. When I do A/B tests between a CD verses iTunes/MacBook via an RCA patch cable through the headphone jack I do not hear a huge amount of difference. A little thinner, a little less rich, but even then I'm wondering if I'm really hearing that difference since the test is not blinded. I certainly chalk that up to my newbie audiophile ears but the point being that with decent ripping software, BitPerfect and this low end DAC I will probably be fine.

I hear reviews saying that the Modi 2 Multibit sounds noticeably better than the Modi 2 Uber while I have heard other reviews say not so much. I'm trying not to get on the upgrade treadmill.....