Of your two options, I'd go with the silicone caulk- but I really have little experience in such things and am truly just talking out of my butt, and I'm no expert caulker.  But, have fun.
TQG
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The Transportable Rig Apple iPod 4G 20Gig --> Canare IC --> Ray Samuels Audio SR-71 --> Sennheiser HD-600 + Headphile Maple Woodie Cups + Equinox Cable
The Portable Rig Apple iPod 4G 20Gig --> Etymotic Research ER4P/S
"Time you enjoyed wasting, was not wasted." -John Lennon
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