I'm considering the same, but will need a long drill bit extender. I've read before people recommended doing this before they were installed, so I'm interested in responses here also.
Certainly you can. As HS said the soil will determine if it works. I drilled a hole through my thought the bottom of one of my winter cover anchor holes. Mu deck had a shallow pooling issue. A decent amount of water goes in to but there is lots of drainage rock to disperse it. Also, our soil is kind of rocky in general and won't erode much with the amount I'm sending in it.
I suspect you just have a very minor amount of water going in it and you'll be just fine.
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