Transaction disappeared in the void...

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If the transaction didn't go out immediately at first, like if you weren't connected at the time, it may take up to 2 hours to resend it.  Long term, it does keep relentlessly sending it.

I'll shorten that length of time in a future version.

You do need to have downloaded the complete block chain (currently 71040 blocks) before you'll see any confirms.  Same with the recipient.