I am going through a painful process of spending $25 on iTunes Match, waiting for it to complete matching, then finding the purchased DRM iTunes tracks, deleting them and re-downloading them so that I have DRM-free 256Kbps tracks.
Most of the songs in my library are non-drm (mp3) and it still took about 18 hours to do steps 1 & 2 (indexing & ?) across 22k songs. Music is stored on a (slow) network attached drobo.
The 5100 songs (25%? Crazy!) that aren't already up there are taking another 24 hours but I assume this is bandwidth dependent.
Crucially, this is all happening in the background, hasn't required my intervention at all, doesn't disrupt using itunes, and once it started uploading everything that it didn't have to upload was immediately available on other devices.
A pretty solid experience, IMO.
Anyone know what happens when the library hits 25k songs???
You probably know better than me, but I thought the 25k limit was for songs in the "uploaded" category (i.e. your 5100 songs). IOW, you would still be far from the limit.
That was the cost of not pirating music.