Got everything all fixed. I did a backup of my save files, reboot PC, completely deleted plugy/d2 and all their folders, reinstall, restore d2 save files and it worked. Still don't know what caused it but I think somehow plugy closed without closing file handle or something so other programs couldn't open them for writing. Also, I learned about Plugy's screenshot folder and it looks like uploading from there fixes my large picture issue.
Anyway, I'm realizing how scary NM can be as melee.
Countess quest kill. My map is trash so I don't know if I want to farm her as much as I said I would, especially because my kill speed isn't great. Maybe after I level a bit I'll re-roll my map.
Found a random Amn rune, made this for bosses and shit.