Well, #1 is certainly possible, though that's all on VGMdb.
#2....not so much. The main problem is I have to be able to have the audio locally or at the very least it should be network-accessible. Unless people can make their collections somehow network-accessible to me, that is. However, please keep in mind the current playlist rotation is somewhere around 20% of the actual available music (I had to run skeleton for MAGFest because I took the archive with me) and then the actual AVAILABLE music pool once I start going through more of it is about 3 times the size.
Once I drop in all of that, it should help a lot, but I wanted to at least test things out with SOME music in place.
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