After rinsing the tomatoes and cutting out the stems, roast them in a 400F oven for 20-25 minutes or until you need them.
Saute 1/4 onion in oil over medium heat for a few minutes. Add 2 minced garlic cloves and saute briefly. Add 1 lb. ground beef and 1 teaspoon salt. Cook over medium heat until the ground beef is lightly browned.
Chop the potato and carrot into smallish pieces (larger pieces will require more simmering time). Once the beef is lightly browned, add the potato and carrot. Saute briefly as you gather the additional ingredients.
For the Tomato-Chipotle mixture, add the roasted tomatoes to a blender or food processor along with 3/4 onion, 2 garlic cloves, 5 chipotles, 1 tablespoon adobo sauce, and a pinch of salt. Combine well. (Here's more info on working with chipotles in adobo.)
Add the Tomato-Chipotle mixture to the beef, along with 1 teaspoon cinnamon, some freshly cracked black pepper, and 1 cup of stock (or water).
Combine well and simmer over medium-low heat for 20-25 minutes, or until the potatoes are cooked all the way through.
Take a final taste for seasoning. I added another 1/2 teaspoon of salt and a heaping 1/2 teaspoon of cinnamon to this batch. Serve immediately.
If you want to serve your Picadillo with raisins or currants you can add them to the beef mixture for the last few minutes of the simmer or you can simply add them as a final garnish.
If you'd like to serve your picadillo over Cilantro Lime Rice, please see this recipe.
Store leftovers in an airtight container in the fridge.