So, i really need to clean out my overide folder of portraits and like things from days gone by and servers for that matter. However, such things as my custom spell icons and the sort i'd like to keep.

A. Is there a way to mass delete portraits?
B. Has a suitable place for overides enmass been made, so that if i do delete the folder, i can redownload the monster and icons i have etc?

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You will need to search on Neverwintervault.net if your gui overrides can be found there.

As to mass deleting portraits, best is to organize the folder content in filetypes. Portraits are .tga files. Each portrait has 5 different sized copies, so just delete those .tga files that have 5 similiar names. Before you do, just make a copy as a back up, so if you delete something wrong by accident you can search for it.