[Milhouse]

I know xbmc isn't caching the fanart I've added myself because when I go into the extrafanart folder and delete everything on my main machine
the art no longer shows up. When I re add it shows up again. So xbmc is reading the local HDD instead of adding to the thumbnail folder.

That is odd, and I can't really explain it, as that isn't really how XBMC is meant to work. Check your xbmc.log for errors (enabling debug may help) - maybe XBMC can't write to your thumbnails folder.

Can you paste the output from "jd movies <moviename>" where <moviename> is one of your movies that has this extrafanart? If it's your tv shows that have extrafanart, substitute "tvshows" for "movies" and upload the output to pastebin...

My music is a smb path. But when I added in fanart myself the browser doesn't give me the option of adding it with a smb path so I have to add the folder. Everything I have is on a flexraid D:/music/artist with full sharing enabled.

Unless you have the Flexraid server mapped as the D:\ drive on all of your clients that D:\ path is simply not going to work. You need to find a way to add artwork that uses the smb path. Unfortunately I don't know why you can't select the smb path, that's maybe something to resolve first. Another option may be to try an addon such as Artwork Downloader which can find and use your local artwork, then set the correct smb path, but resolving your issue with smb browsing is probably the first step.