@edsnova
Whoa..... I'm prob'ly a shape-shifting short-shifter and didn't even know it!
I thought of that a long time ago, too, and replaced that little rubber booty-thing with a new one the last time I had the engine out but God knows, it could still be leaking there.
Honestly, we're not talking a big leak from the e-brake hole. More of an annoyance and you never feel anything when the top is down, of course, and I would probably spend way more time trying to find the source(s) than it's worth.
BTW: A comment from @DannyP way up above got me thinking, too, so I researched it: That is, that some silicone caulks contain acetic acid as a partial curing agent (and to make them stick better) and that stuff can attack and be corrosive to sensitive metals (Think electrical connectors in a car).
So I found a decent article about it HERE. In summary, I found, as Danny alluded, that there are two types of Silicone caulk: Acetoxy Cure (with the bad-for-your-connectors Acetic Acid) and Neutral Cure without the Acetic Acid and safe to use on connectors (and is actually a very good insulator).
The silicone caulk I've always used is GE Silicone I or II because that's the most prominent at Home Depot (and also gave me the most color choices), so I looked up the specs and Lo and Behold, it is a Neutral Cure product. So not only is it OK to use in Pearl, all you guys (I'm looking at YOU, Dr. Clock) who've used the GE stuff or something similar to goop things up and make them weatherproof are all safe. If you used "Joe Slunks super-sticky inferior grade sorta-silicone smells-like-vinegar caulk" instead, well, you might want to rethink that.
Thanks to Danny for pointing that out - Those retired Verizon guys are pretty with-it. The vinegar smell is a dead give-away that you're usin' the wrong stuff!