Thanks everyone. I am trying to make a Friday fish fry dinner with family outside of Milwaukee, otherwise will probably fly Saturday morning. My aunt and uncle are older and they eat on the early side. That's why making the connection would be critical.
I appreciate knowing that DTW is fast on handling baggage. That helps because I can move a lot faster if all I am carrying is basically a laptop bag. Also knowing the BUF flight usually comes at Terminal B helps. If it was likely to come into A I might be more inclined to chance it.
I like the Delta option as both legs are actually "F" connections - and avoiding ORD. There's a United flight with a 57 min connection through ORD, that might be safer. Just have to suck up the ~ 2 hour BUF to ORD leg on the ERJ145.