Waiting on Wednesday! PS: I NEED HELP!!

There isn't a particular book I am waiting on, however I am waiting on some very book related business. My ereader will not let me add books using the Kobo Desktop app. I bought 7 books which I want very very badly to get on there (with the first 4 Song of Ice and Fire being the main ones) but when I connect it, it says it syncs, but the books are not there.
I really don't want to have to do a full reboot, because I have over 100 books on there right now (still says there is tons of room to add more tho). I am willing to do this if necessary, but I want to finish the library book I am reading (The Host) first, so I don't have to go on the wait list again.
I had received a bunch of e books from a friend that she had bought for a different reader and added them to mine using Calibre, could this be what is causing the problem? If it is, is there any way I can add the Kobo books using Calibre to beat this issue? I want to keep borrowing e books from friends and from the library (cause books are expensive!) but not if its going to mess with my ereader.

Computer knowing friends - please help me!! I would be sooo grateful!!

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