This will be a Mac thing for sure.... you need to reset the permissions of the folder you are d/loading to..... the message is a bit obscure but it also means "could not write to"... check the folder permissions with cmd-i, you may need to go up several levels!!
Thanks for the quick response Geoff but I checked my permissions and they're as I would expect them.
My photos import to /Users/[USERNAME]/Pictures/[YEAR]/[MONDT]-[DAY] and my 2014 folder has the following permissions:
Terriann (me) - Read & Write
staff - Read only
everyone - Read only
I updated the folder's permissions to be Read & Write for Terriann, staff and everyone and I still get the same error message.
Sometimes the destination folder accidentally changes. Make sure you are checking the permissions on the folder that is actually specified in the Destination panel of the Import dialog box. Do not assume that the folder you used in the past is the one Lightroom is using, the permissions on that folder are irrelevant.
While "permissions on that folder are irrelevant" left a bit sour, you were correct. Somehow the destination folder had changed during one of my previous imports, when I corrected the destination it imported correctly. Now I feel rather foolish :/ I must've accidentally changed the destination then scrolled back up cause it was never clear in the other imports that the destination folder was ever different!
I had even downloaded the log and there was nothing there that caught my eye either. If the log text file had said "Could not write to /some/other/folder/not/2014/like/you/think" that would-a made it easier for me diagnose this issue