Season chicken generously with salt and pepper and set aside while you prep the vegetables.
Peel husks from tomatillos and rinse them under warm water to remove sticky residue. Cut tomatillos into 1/2-inch pieces (or thereabouts—they’re spheres, after all).
Rinse potatoes. You can peel them or not, depending on how thick the skin is, then dice into 1/2-inch pieces (same caveat about non-square shape of potatoes).
Peel and chop onion.
Chop the habanero or other pepper. Remove the seeds for the habanero—they’re hot—and chop finely. If you’re using a jalapeño, you can remove as much of the seeds and ribs as you like. For the canned chipotle, chop the whole thing. NOTE: whatever pepper you’re using, wash your hands multiple times and don’t rub your eyes.
Put the bacon in a large, cold lidded sauté pan. Turn the heat to medium-high and cook, turning frequently, until crisp. Drain on a paper towel-lined plate. (You’ll only use 2 strips of cooked bacon in the dish, but you want the bacon fat. You can reserve the other 2 cooked strips for a “future use”—in our house, that means eating it now.)
If the bacon doesn’t create enough fat—ours didn’t—drizzle in a little olive oil to barely coat the bottom of the pan. Add the chicken, skin side down, and cook until nicely browned, at least 6 minutes. Turn the chicken, reduce the heat to medium, and cook for 4 minutes. Transfer chicken to a plate and set aside.
Add onion, garlic and pepper (not the canned chipotle, if using) to the pan and cook, stirring for 1 minute.
Add tomatillo to pan, stir to combine everything and cook for 5 minutes.
Add potato, canned chipotle (if using) and 1/4-cup of cilantro to pan and stir to combine.
Add broth, water and oregano to pan. Crumble up the bacon and add that, if using. Stir and scrape up any browned bits. Bring to a boil over high heat, then nestle in chicken pieces, reduce to a simmer and cook, partially covered, for 25 to 30 minutes, until chicken is cooked through and potatoes are quite tender. If the sauce cooks down too much, stir in a little water.
Conversely, if the sauce remains too watery, thicken it slightly with cornstarch: remove the chicken to a plate, then mix 1 tablespoon of cornstarch with 1 tablespoon cold water in a small bowl. Spoon a little of the sauce into the cornstarch bowl and stir it in. Do this a few times; you are warming the cornstarch mixture so it doesn’t clot up. Gradually stir it into the pan to completely combine and cook for 2 to 3 minutes to allow it to thicken the sauce.
Serve. Spoon the tomatillo/potato mixture into shallow soup bowls. Top with a piece of chicken, then scatter chopped cilantro over as a garnish. Besides a knife and fork, make sure everyone has a spoon to scoop up all the sauce!