Core and slice tomatoes, add sugar, and muddle lightly. Add ginger and chile. Cover and let rest for 1 hour.
Add chives, peppercorns, and lemon zest to tomato mixture. Pour into a double boiler. Bring water to a boil and immediately reduce to simmer, as low heat as possible. Cover tomato mixture with lid to retain moisture. Simmer for at least 1 hour.
Remove from bath. Strain contents through a chinois or the finest sieve you have. Harvest all juice possible, and discard the pulp.
Add vinegar and hot sauce to strained juice. Whisk thoroughly. Refrigerate until cool.
To mix your drink, choose your poison and use a 2-to-1 tomato mix to alcohol ratio. Build the drink with ice cubes, alcohol, and tomato mix. Add agave syrup, lemon juice, and bitters.
Roll the drink (pour from glass to glass, rather than shaking or stirring). Garnish with pickled vegetables.