(1) My laptop is a little iffy. Not as iffy as the previous laptop was when I bought this laptop; more like about three months before that point. Possibly six -- my memory is a little hazy.
(2) I will replace my laptop with another Macbook, but the new Macbooks no longer have optical drives. If I am going to rip all my CDs, the Time is Now.
(3) I wound up with an unusual amount of childcare this summer.
(4) A lot of the other physical->digital transition stuff in my life has already been dealt with.
In order to transition from the existing laptop to the new laptop, I needed to get the contents off of the current one and onto the new one. And since the biggest item on my laptop is my iTunes library, it made sense to tackle that first, by moving it to an external hard drive (which I already had, from the previous laptop transition, and at 500 Gig, seemed big enough), and then ripping to the external hard drive. Signing up for iTunes Match Just Made Sense, to then make all that music available on all the mobile devices.
I did not think about Google's service at all. I thought about Amazon's service for about a nanosecond, then decided against it. The playlist issue which seems to be the biggest problem with iTunes Match is wildly irrelevant to me. I'm slightly concerned about the losing-explicit-versions problem, but not very. I assumed matching would work well for me, and thought it was working 100%, but it turns out not so; more about that as I figure it out.
I did not know about the device limit (10 devices to an iTunes account, sort of), and it may have bitten me. Because no-longer-in-existence devices were still using slots, it may have caused the catalog to not keep up on some of the devices. Certainly, once I freed up slots, the mobile devices seemed to keep up better with updates to the cloud.
Using a Smart Playlist (things I knew existed, but didn't know what they were called or how to make them, five minutes ago), I currently have just under 900 songs that uploaded (rather than "Matched" or were "Purchased"), out of a library somewhat over 6000 songs. Some of these are a little unusual (the soundtrack for Plants vs. Zombies), obscure (two of Oren Rosenthal's discs -- he does the music program at my kids' preschool). Others are Known Problems (Jimmy Buffett is apparently a little infamous for not matching, even when it seems identical with what is for sale in the store). Quite a lot are Greatest Hits collections from the somewhat distant past (Eartha Kitt, Lovin' Spoonful <-- you only think I'm joking). Elvis Costello is massively overrepresented, which I attribute to that notorious label problem.
I do have examples of the half-the-album-matched-and-the-other-hal
All in all, the project is going pretty well. There have been minor issues that led to me understanding fairly basic aspects of how iTunes, the store and so forth work that I probably should have learned before now, so the greater your knowledge before you start, the better. In many ways, this has been an exercise in the Benefits of Being a Not Early Adopter.
ETA: Of course as soon as I post that, I realize that iTunes Match is completely stalled. After trying a whole bunch of things, I resorted to the SC Info deletion trick, which seems to have fixed it (altho it sure confused the store, which is probably the point -- forcing it to retry from before wherever it got confused). The only one left in "Waiting" status after that was a Purchased track which has since undergone a name change in the store (it's an explicit track by P!nk). I finally just said fuck it and deleted it since it's really already in the cloud anyway (after all, it's a Purchased track; Match just couldn't seem to figure that out).
I then started ripping more CDs. More problems. I am not finding this at all amusing.