Guys Winter is so awesome. I was going to make you a JibJab card but the only free thank-you one they had was like... a creepy lemon man jumping around... *shudder*. Anyhow, to business--
I think it would make more sense for "Pokémon Black & White 2 Versions" to be "Pokémon Black 2 & White 2 Versions"
Also it seems inconsistent to have "Pokémon Black & White Versions" and then "Pokémon Diamond/Pearl/Platinum Versions." Should have either all & or all /. I'm indifferent between the two, however.
At your question about Route 2 and 3 in the second spoiler tag, Route 2 and 3 have the same music in B/W, but they both change depending on the season. So that suggestion is saying "Let's switch the current name of "Route 3" to "Route 2/3 (*season*)." Problem is, I can't identify which season DrP made in that arrangement. I'll send him a PM.
@comingaflame's suggestion, I don't think it's necessary to place the series titles in there. While these tracks are based on tunes from past games, they are commonly remixes and belong in their own section with their simple title-- the title of the song.
@Bubbles' suggestion, I absolutely agree that we should use titles for every place it's played in-game. I've missed a collection of arrangements on this site because I didn't know they also played in a different location.
I will check the Castevania PDFs
Also, you have two "suggested by Winter, me!" sections in the OP