Toro rule of thumb:
A) I don't care about your gameplay woes. This is entirely song based.
B) Song > lyric meaning > video for rankings. In general videos have the least impact for me. There is one golden exception for me in this list. I'll mention it when it comes up at the end.

Top 5:
1) Unhappy Refrain - Powerful and good variance/range musically, may be miserable to play but IDK. :V
2) Senbonzakura (I'd heard the original before this version. Both versions are excellent.)
3) Dream-Eating Monochrome Baku (See above. I like Diva version here slightly more, like original of Senbonzakura more, but neither's a major change.)
4) Urbandonment (Voice tuning is right on, lyrics are good, and I really like the song in general. Basically this feels like a really natural song to me, and it's stuck with me.)
5) Weekender Girl (I tend to call songs like this cheerpop, and this is very good in this vein.)


V. High:
6t) Tengaku (BURN IT ALL DOWN - less technical vocaloid work but very good song and excellent thematics. Dropped from my top 5 on a few relistens, but not far - this is basically the definition of very excellent ... what's the word I'm looking for here. "classical Vocaloid"?)
6t) Freely Tomorrow (Cheerpop v.2. Used to be at 10, relistened, decided to pop it up to tie Weekender Girl)
6t) Rin-Chan Now (In fairness, I didn't want to rate this, but Tonfa requested. Anyway this is a comedy sketch to me and not a song, and a pretty funny one at that. Would probably sink into something vaguely creepy except the ending is Rin launching the singers into outer space.)
*)
9) Ashes to Ashes (Hella dramatic, Kaito's voice IMO fits fucking perfectly here (I am used to hearing him on creepy/dark songs though.))
10) Tokyo Teddy Bear (Reminded me heavily of a song I love - https://www.youtube.com/watch?v=O0TtDeDiHcE - similar aesethic, matching visuals at a point, both do their buildups very well.)
11) World's End Dance Hall (Original > Kaito/Len > Miku/Luka) (Okay. So, I heard this before watching the Diva version, and I love the original version. Saw new video, went O.o)
12) Time Machine (Reminds me of the Kagerou Project songs, which is a compliment. Does some things a bit better, even, but I... IDK. Feel like it misfired on some of the higher notes.)
13) Odds & Ends (Very good, tuning felt right on top, but lacked some sort of punch to carry it higher IMO.)

14t) Kagamine HachiHachi Flower Fight (This should have been longer. Probably the one and only grief I have with it - there's more that can be built on the song and should have been, IMO.)
14t) Remote Controller (Diva vers.) - This is a really good version of the original, which has too much non-singing - it's obvious where the cuts were made in this version, but they're good cuts IMO.

Solid:
16) Tell Your World (Slightly less fond of this as cheerpop, in part because it starts slower/more serenely.)
17) DYE (It's... bizarre. It does well for that. Bumped to near-top thanks to a relisten - it doesn't feel like it earns the abrupt finish but see SnowFire, minus that I like the stuff above more.)
18) Sadistic.MusicFactory (A fun song but it keeps getting overridden mentally by https://www.youtube.com/watch?v=fdS854pzkS0 )
19) Hm? Ah, Yes (Okay, yeah, I undersold this IMO. It's a very solid song, if shorter?)
*) World's End Umbrella (Original) (Diva version's further down. I... really didn't like the remake.)
20) Secret Police (Fun but needed a stinger or someplace to go with the buildup.)
21) Sweet Devil (Just wound up unimpressed at all. EDIT: Tonfa was right, this has grown on me. oddly enough I think the video hurts it, been preferring to listen to it w/o video)
22) Nostalogic (Very good when Meiko's singing, good outro, needs less time between those two points. Video is sort of fanservice-y and not my speed/not that engaging which is the main differentiation from it being here or being up with the 6s. EDIT: Relistened... god, the intro. Starts promising but then it gets to M-E-I-K-O and I lose it. Also, the scratchy starting voice/tuning only coming up right at the start... I don't know.)
23) Nya (Apparently this song is horrific to play. I believe it. I also don't care, it's hilarious. Would explicitly not get into a playlist unless it was a huge playlist designed for working with background music.)
*) Remote Control (Original)
24) Negaposi*Continues (On a relisten, this got hit hard - it just doesn't sell me well here. It's good. but it's not... it's... how do I put this? It relies on repetition and isn't as catchy as Secret Police.)
25) ACUTE (Needs more vocal variation)


Decent Enough To Bad
26) Summer Idol (It does the intro just right, but the rest of the song languishes a bit.)
27) Stay With Me (The vocaloid's voice is not well tuned for this, IMO. If you can get past that? This could be awesome - it does everything else really, really well. But the vocals are jarring enough for me to not be able to put it higher.)
28) Melancholic (Yeah, the recording from the game has weird static spikes not in the song itself, oddly. This is a decent enough song, if not really my rolling speed.)
29) Cat Food (It... earns this mainly on a solid start, the song gets worse/more generic/more all over the place as it goes on)
30) The MMORPG Addict's Anthem (Just really doesn't grab me at all, sadly.)
31) MonochromeBlue Sky (Cool video conceptually, but the song doesn't do it justice.)
32t) What Do You Mean?! (This should have done better. But I don't like the tuning on the vocaloid here, feel like the repetition hurts,... it's a collection of weird decisions that wind up turning me off of the song p. hard.)
32t) BlackRock Shooter  (This is basically my line of averageness.)
34) God-Tier Tune
35) Fire@Flower (Has managed to interest me less and less with each listen. Not a good sign.)
36) World's End Umbrella (Diva vers.) (This version... just suffered in transition. A bunch of small changes to tuning, to the instruments clashing at the start... it just doesn't work, IMO.)
37) Continuing Dream

Why:
38) Glasses (Okay. See that *) right below 6t? That is where this song -should- be. Its construction is excellent, it's very melodic, Luka fits perfectly with it, and a bad video/nonsense lyrics would earn it that spot. Instead it's male gaze wish fulfillment bullshit shoehorned into, and perfectly ruining, what should be a good song. There are points where I went "Okay, this or that design is explicitly fanservice". Okay, whatever, I both expect that and can generally zone it out (see Freely Tomorrow). This song is "I feel like I just stumbled into someone's hidden Youtube fetish playlist of girls with glasses on and a creepy dialogue of what they'd do to said girls over perfectly good music". You can make an argument for Rin-Chan Now being creepy, but... it comes off as a comedy sketch in which the target is not the joke but is rather the one who has to deal with this shit, which is almost a fucking subversion of the trope. This song just. Argh. I can't.)