The card says "at the beginning of upkeep you may discard a card to untap enchanted creature".
Can i repeat this process (by tapping untapped creature to activate ability and then discarding a card)?
No. Here's the Oracle text:
"Enchant creature
Enchanted creature doesn't untap during its controller's untap step.
At the beginning of the upkeep of enchanted creature's controller, that player may discard a card at random. If he or she does, untap that creature."
One trigger, one chance to untap.
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