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It most likely has to do with the size of the ring tone. I can't remember the limit, but I know there is one with WM 6.1 that was not there before. I had to use an mp3 editor and cut the ring tones down to 30 seconds, set at mono. This takes them to less than 300 kb. ALL my ring tones are on my SD card and every time I hard reset my phone, I can reassign them no problem. I also think there is a post like this in XDA, a tweak I think that removes the size limit. I don't know if this matter, but they are stored on the card under: storage card/my documents/my ringtones. That may also have something to do with it. {{EDIT}} I just moved and renamed the folder with my ringtones and my phone still found them. So it must be the size of the filter
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~Never pick a fight with an ugly person, they've got nothing to lose.
Robin Williams
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