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Kobo Original Cannot Upgrade

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Im hoping someone out there can help me. I've a Kobo Original that I've just unburied from the bookshelf. I wanted to load a few new books for vacation. I brought the first one and I couldn't get it to sync onto my Kobo from Kobo Desktop. I read that I might need to upgrade to Version 1.8, so I did so - still no luck. I read that I might need to delete my original desktop and download the new one from the Kobo website and try upgrading again - still no luck. Every time I do the key combination to 'reset' all I get is the blank screen and nothing happens from there. I've left it till the battery goes flat - so Im not thinking it will happen instantly! I've tried several times and it just wont work! Can anyone shed any light?
I should probably mention that Im using Mac too!

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