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In the opening post:
i interprete that "(no system timestamp here)" means, that last modification time is not usable. In real life sometimes files get touched by "accident". Or by "transporting" it...

Just use simple commands. ls, grep, sort, tail and xargs.

ls | grep "\.dat" | sort -r -t. -k3,4 | tail +13 | xargs rm

Just enhanced your sort command by reversing the sort order, to get the...

Which of the two involved devices throws the "I/O Error"? If you ran out of disk space you wont get an "I/O Error" message.
Either the USB-stick is buggy or your disk has defective sectors.

Btw:...