Fixed for all except Air Raid and Skydive -- I've counted their repurposed Legends figure under Generation 2 (1995).
Fix'd.
Hence the "True" Classicsverse & "Faux" Classicsverse categories -- if people want to get picky and overlook repaints from other toylines that have been repainted and chucked into Classicsverse as opposed to those that have been purpose-designed for Classicsverse, then they should be focusing on the "True" Classicsverse figures marked with
[+] (or their repaints marked with [+]).
Anything marked with [/] are "Faux" (false) Classicsverse; i.e. non-Classicsverse moulds that have been repainted and thrown into the Classicsverse line by Hasbro. These toys may be widely considered to be not 'real' Classicsverse toys by many collectors and only really count because of Hasbro marketing, but otherwise don't really feel like they belong in the Classicsverse line.
Trying to 'count' anything is jolly hard because everyone has a different opinion on what should and shouldn't count. And unlike the Universal Counting Method for toys, I am
NOT even going to try to come up with a general consensus for what toys should and shouldn't count for Classicsverse. I've tried to include every character who's ever had a toy incarnation that HasTak have marketed under CHUGGURT as well as those which they haven't but their marketing or history lends some ambiguity that there might be a case to argue for them to count (see TF2010 and ROTF Bludgeon discussion below).
I've tried to point out which ones are toys that are purpose-made for Classicsverse, which ones aren't, which are repaints of what and so forth and people can just decide for themselves which ones they want to count or not.
Go to brick and mortar stores and look on shelves.

Looking at other people's collections is a good suggestion... try before you buy.

Maybe arrange for 'show and tell' at fan meets
I've tried to eliminate fan bias as much as possible - that's why I'm not including arbitrary "stand ins" (i.e. non-Classicsverse toys that people personally decide to repurpose as Classicsverse, e.g. Music Label Soundwave as Classicsverse G1 1984 Soundwave, Movieverse Axor as Classicsverse Axer etc.).
Anything that's listed as having a Classicsverse toy is there because they have a toy which HasTak have explicitly marketed as Classics/Timelines/Henkei/Gentei/Universe/Generations/United/Reveal The Shield or other similar lines that are part of what we call "Classicsverse". There are some which are ambiguous, particularly those from Hasbro's label-less Transformers 2010 line, and others like ROTF Bludgeon who was ultimately a ROTF toy but at one stage was considered by Hasbro to be a Classicsverse toy (thus some fans might argue "prior intent"). And even there I've labelled with with [?] to denote the ambiguous or debatable nature of their classification as Classicsverse.
Any toy with
[+] or [+] are definitely Classicsverse. Can't go wrong with those IMO.

Okay, I've now redefined the rare figures...
[R] = bloody rare "True" Classicsverse moulds, e.g. United Frumble (original mould made for Classicsverse)
[R] = bloody rare "True" Classicsverse repaints, e.g. Shattered Glass Thundercracker (repaint of Classics Starscream mould)
[r] = bloody rare "Faux" Classicsverse repaints, e.g. Timelines Double Punch (repaint of Energon Scorponok)