Update 2: In the hardware log I found that the root partition over the last year went from a fairly steady 50-60% usage to 90-93% usage between the 1st of the year and 1/10/2016... and now has stayed there. Which is most likely why my up2date will no longer work. I deleted most of the auto backups... which has helped get me a small amount extra space on root (checked with the df command as I deleted them). But is there anything more I can do to recover some of that 30% of space it used to have before the 1st of the year? Thanks again!
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