As far as drilling with a dremel - definitely do-able, I just did a 1 1/2" bulkhead into 3/8" glass, 15 minutes. Don't push on the bit, let the dremels weight do the work.
Serlunchbox - grab yourself the free copy of sketchup and draw up what you mean... Personally I'm not following - I think you're talking about just drilling and using a stand pipe?
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