1) the recognition by cddb of home burned CDs is very hit and miss - sometimes it happens, other times not!
2) Now I am transferring vinyl to my PC for onward journey to the Brennan, I create flac files and insert the tag info myself. I use Audacity to record the vinyl (on a Linux computer, but there are versions of it for Windows too) There have been programs i have used in the past which purport to separate the tracks - but I found them very unsatisfactory. They work by detecting a pause in the sound - which fails if a track has "silent" passages in it, but also where tracks merge into one another without a pause. The other benefit of this more "hands on" approach is that it allows me to edit out cracks and blips (which a lot of my albums seem to have!) before uploading to the Brennan. So in my experience it is quite a lot more time consuming than CD ripping!