Always gotta push the limits…
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As a dirty vodka martini fan, I would try most of those. Pretty sure the brine used in the one I had at Eastern Standard a few weeks ago was clarified.
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I rarely order a dirty martini, since I’m solidly in the gin martini camp, and find that most brines will overpower the gin.
Vodka only if dirty, and then all bets are off. There’s a distillery nearby that makes a vodka martini with their own vodka, spicy pickle brine & a spicy pickle garnish that is weirdly addictive.
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I occasionally enjoy a dirty Gibson.
Quite some time ago we had a couple Five O’Clock Somewheres with a New Yorker who always ordered the Martini with as many olives that the toothpick could hold, even sometimes receiving an extra skewer-full. The practice was to stir the drink with the skewered olive on the tip, sip, savor, chomp down the olive. Rinse and repeat . . .
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I was with some friends in a bar and one ordered a glass of olives with gin poured over it. And got it.
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That’s what I do, too. I use bamboo spears that are longer than toothpicks, so I can get more olives on them. I wonder how much extra sodium I’m getting…
One of our favorite breweries in town has wonderful lemon-marinated olives. I could eat the whole bag, no martini needed! 
Aha!
