So, I disassembled and cleaned the taco plate per Mark's suggestion above, as I had not done this previously. Before cleaning it, I thought the plate was painted black.
WRONG
As I soaked it in carb cleaner and scrubbed with a nylon brush, I came to see that the color was grey. Over the next 40 mins or so I removed all kinds of past sins -- gasket maker, papery stuff...who knows.
I then put a thin coat of permatex on either side of the sealing ring for the temp probe itself. I used no other goop.
I reused the gasket between the plate and cover since I didn't have another one handy and it was in fine shape -- only been installed for a few days, after all.
I used new copper crush washers under the bolt heads, and reused my 4-day-old orange o-ring.
Ran it up on stands for a half hour, ran it into third gear a few times during that time, turned it off, came back after an hour...
Dry as a bone underneath
Looks like I'll be taking it to work tomorrow!
(provided it doesn't snow)