Heat a heavy, large casserole or Dutch oven (not nonstick) over medium-high heat. Add 1 tbsp. oil. When hot, add 1/5 to 1/4 of the beef. The first piece should sizzle when it hits the pot; if it doesn't, remove it and wait for the oil to get hotter. The pieces should not touch—you want plenty of room so the juices will evaporate quickly and the meat can brown. Cook until well browned and a bit crusted, about 5 minutes each side, adjusting heat so meat sizzles but does not burn. They're ready to turn when they release from the pot easily. Transfer meat to a bowl and repeat with remaining meat and oil, for a total of 4 or 5 batches. This takes about an hour when done properly.
Preheat oven to 350°. Add bacon to pot and cook until fat renders and bacon starts to brown. Transfer bacon to bowl with beef. Add onions to pot and stir in 1 tsp. salt. Cook, stirring, until onions begin to soften, about 2 minutes. Transfer onions to bowl with beef. Add flour to pot and cook, stirring, until it starts to turn golden and smells faintly of piecrust, about 2 minutes. Add smoked paprika and chipotle powder and cook, stirring, until fragrant, 30 seconds.
Add wine and increase heat to high. Scrape up any browned bits from bottom of pot. Add reserved beef, bacon, and onions. Bring mixture to a boil. Cover and bake until meat is tender, about 1 1/2 hours.
Return pot to stove. Add potatoes and bring to a boil. Add carrots and bring back to a boil. Adjust heat to maintain a simmer. Cook, uncovered, until vegetables are tender, 30 minutes. Stir in butter and add salt to taste. Serve hot, garnished with blue cheese, pepper, and chives.
Note: Nutrition analysis is per 1 1/2-cup serving.