Oldest you can get is the original RAITA sketch that spawned Katawa Shoujo. Came from the back of a Nausicaä doujin he made.
https://cripple.booru.org/index.php?page=post&s=view&id=1570
Colored in by fans: https://cripple.booru.org/index.php?page=post&s=view&id=1
You can look through the dev blogs to see how their art of the characters evolved over time.
http://katawashoujo.blogspot.com/2011/11/shizooooon.htmlhttp://katawashoujo.blogspot.com...h-direction-complete.htmlhttp://katawashoujo.blogspot.com...h-direction-complete.htmlhttp://katawashoujo.blogspot.com...h-direction-complete.htmlhttp://katawashoujo.blogspot.com...ase-of-emi-ibarazaki.htmlAlso just searching through the devs art will get you some of their earlier art pieces. Interesting one for you may be 'Kekekeke' who designed the sprites for the Grid1 demo early on in Katawa Shoujo's development.
https://cripple.booru.org/index.php?page=post&s=list&tags=kekekeke
Sure you can find a rip of the Grid1 sprites somewhere out their too if you want.
As for pure 'fan' fanart, it's hard to say. With the death of the Shimmie a lot of context for art has been lost but you can use the 'Wayback Machine' to see how the Shimmie was. You can also look through the forums to see older fanart. Unfortunately some used now obsolete image hosting sites, but there is still a decent amount to browse.
https://ks.renai.us/
Check out Gamera. A very interesting case in KS history since they made fanart based purely on the RAITA sketches before the threads on 4chan that started the whole project.
http://gammatelier.free.fr/page.php?art=amp_classroomHope this is helpful.