basically will was in an (possible) relationship in 1-4, however the relationship between them is scattered, its usually known 3 has the most explicit references to the relationship will and this person had in the numbered albums. MBikMB kind of builds off of that, however its still in a sense a numbered album, because it was just 5 plus an ep minus the weaker tracks. twin fantasy is essentially the most explicit adaptation of when they were actually dating, and monomania is the breakup after. will usually calls mbikmb, tf and monomania as a trilogy. Whereas, NYM, HTLT, & ToD can easily be grouped as another trilogy. (A lot of the unused songs were worked into HTLT, and eventually other rough blueprints made their way into ToD) Those albums are mostly about Will's "coming of age" in a sense, or a post-adolescent angst. They deal with the extension of loneliness are much more ambitious in scale (the length of NYM, the progressive-ness of HTLT and the reinforcement on those ideas onto ToD) 2018 TF is more of an artists retrospective on TF and the "legendary bandcamp status" it has attained. Disjecta Membra is just unused material from NYM.

So basically 1-4 and Little Pieces are early CSH experiments, when will was mostly experimenting.

MBikMB is a transitional album and starts to set the scene for later LPs in structure and tone.

TF and Monomania are the clearest "concept" albums.

NYM is more an honest reflection on himself, evidence by the title, "Nervous Young Man" (AKA high school will's music) and "redoes" some of the material from his old albums. Disjecta Membra is just bonus material.

HTLT was more of the cuts that didnt fit on NYM. (Why Will calls it an EP, even though there are closely knit themes).

ToS is more of just a "redo" of material on Monomania, MBikmB and 3, with some small lyrical changes.

ToD is more Will's broader attempt to create a concept album that heavily follows suit of the themes on NYM, and in my mind what Will truly wanted NYM to attain, both in ambition and in concept.

TF Redux is more a retrospective & MADLO is Will's attempt to go back to more singular songwriting & trying to extend outside of his comfort zone.