Alright, did some playing and leveled up my Int, seems to have let me get passed the block. I was at 7 and leveled to 8 and now I can upgrade the items I could not previously.
Ah okay, just installed an AMD SMT fix and was worried that might have been the cause.
But yeah, there are a few already. Nothing really "major" just yet. Mainly fixes, cheats & presets.
I don't think you can, but really I never tried looking. It seems to pop up when you for sure don't meet the req to wear the item. But it also pops up for other items that I already have one.
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Did you have any mods installed?