Mince the garlic cloves finely and set aside. Juice the limes into a small bowl—you should have about 3 tablespoons of fresh lime juice. Finely dice the red onion and place in a separate bowl. Halve the cherry tomatoes, scoop out the seeds with a small spoon, then dice the flesh into small, uniform pieces. Seed the jalapeño by cutting it lengthwise and scraping out the ribs and seeds with a knife tip, then mince it finely. Having everything prepped and ready will make assembly quick and ensure even distribution of flavors.
Cut each avocado in half lengthwise, working around the pit, then twist the halves apart and remove the pit with a spoon. Scoop the flesh into a medium bowl and add the minced garlic, lime juice, ground cumin, and chipotle powder all at once. Using a fork, mash the avocado to your desired consistency—I prefer leaving it slightly chunky for better texture, but you can make it as smooth as you like. The lime juice will prevent browning and brighten the flavors, while the spices bloom when mixed with the warm avocado flesh.
Gently fold the diced red onion, cherry tomato pieces, and minced jalapeño into the mashed avocado mixture from Step 2, stirring just until evenly distributed. Add the extra virgin olive oil, kosher salt, and freshly ground black pepper, then taste and adjust seasonings as needed—the lime juice and salt should really pop the fresh flavors. I like to taste before serving because lime and salt levels can vary, and a final pinch of either can make all the difference in the final result.
Transfer the guacamole to a serving bowl and serve right away with tortilla chips, tacos, or as a topping for other dishes. Guacamole is best enjoyed fresh, as the avocado will continue to oxidize over time despite the lime juice protection.