Issue 1: Lossless formats
The first issue I considered is which lossless format to use. AFAIK the most common ones are ALAC and FLAC. Some other formats may have both lossy and lossless variants.
Personally I can convert to either ALAC or FLAC, but since I use an iMac frequently the "obvious" choice is ALAC. This gives immediate iTunes compatibility, and it seems to be compatible with my Squeezebox kit too.
I assume that if necessary I can convert from ALAC back to FLAC, so there is no harm in choosing ALAC at the outset.
On the other hand, some people may recommend FLAC, which for me would give an immediate compatibility issue with iTunes, though there are ways round, for example using Fluke - http://code.google.com/p/flukeformac/
Some people may find FLAC is immediately more convenient for them.
Can I assume that, for me, that ALAC is really the way to go?
Issue 2: Choice of playback device/system
Following Issue 1, it seems reasonable for me to stick with iTunes for playing some of the ALAC files, and my Logitech kit works with those.
Some people - particularly those who don't use iPods or iMacs, but who are using PCs may wish to use other players and playback devices. It is quite possible that some players and devices won't play ALAC, in which case that either restricts the players to be used, or step 1 - choice of format - needs to be changed.
Issue 3: Converting between lossless formats
I assume that there are good converters which can convert from ALAC to FLAC and/or FLAC to ALAC. While I hope that I don't need these initially, at some later stage it might be necessary. By then I would hope to be able to do batch conversion from files on one drive to another.
Is it easier going one way rather than the other? Are some tools easier to use than others? Recommendations!
Issue 4: Generating track metadata
Most tools, such as iTunes etc., will try to match CD tracks against a CD database - often the Gracenote one.
This clearly saves a lot of time, and in many cases will also cause the artwork to be located - not sure how - but it does, and can appear in a user interface, such as for SqueezePad.
Some rippers are not so good at this - for example when I ripped a CD using Max for MacOS the other day, it couldn't find the data for one CD, so I had to partially enter it manually, and all the tracks were given numbers - relative to the name I provided.
I don't know how easy it is to modify such metadata afterwards, but in the first instance it helps to get as much accurate data as possible. The time taken to enter/correct such data can easily approach or exceed the ripping time. If only a few CDs aren't recognised this might not be a problem, but it could be if this happens relatively often.
I noticed a few years ago that some tools use different databases, and give different results. Are there any preferred tools/databases?