Bear with me on this long post - there is a point...
I did 5 AUS-DFW-SJC-ORD-DFW-AUS runs in a row a few weeks back, and on the 3rd or 4th one (it's a blur), My DFW-SJC flight was late getting in, which caused me to miss my SJC-ORD. The AC agent had already booked me on the next n/s back to Austin since, that is, of course where my final destination was. After explaining to her that I really needed to be in Chicago to meet with a business associate, she gave me a "uh-huh", and started clicking away at her computer, then told me to go ahead and have a seat and she'd work on it. Imagine my surprise when she brought me back boarding passes from SJC-LAX-SFO-DFW-AUS! I I gave her a dumbfounded look, and she said something along the lines of "I looked at your profile and it looks like you're trying to maximize your miles, so this was the best I could do".
I was shocked. Needless to say, there are some sAAvvy AAgents out there who know what we're up to and don't seem to mind helping.
I'd say if you miss your DTW connection, you'll be just fine. Just find a cooperative agent who isn't too harried or call your elite desk and they'll help you out...