I have a black, internal overflow with two bulkheads coming out of the rear of the back glass. Before I painted the glass black, I temporarily installed the bulkheads and wrapped them with painters tape. Then I sprayed several coats on the back.
Turned out great. You want a really good seal between the bulkhead and the glass. I didn't want any paint under the bulkhead. Good luck.
And... you're not anal at all. I think about this stuff all the time!
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