I realize this doesn't quite answer the question, but I went the other way, and went from AA EXP to DL PLT when the EQD upgrade priority was announced. [I dropped to DL:Gold this year due to an illness in 4Q17.] My upgrade percentages on DL are fantastic on CR9/E175s, especially to NYC/SLC, horrible to/from MSP or to ATL, but decent on the late night ATL-ORD/MDW flights.
What is relevant is this: As EXP/PPRo, as long as you leave DTW before 2pm you should be ok to PHL/CLT/DTW. You are flying against the stream. For example, tomorrow's 6am DTW-PHL is still only filled to 3/11 on an E90. Granted it's the day after the holiday, but next Sunday go check next Monday's flight and you'll get a good feel for it. ORD will be a problem because AA is almost all CR7 which means that IRROPS and lousy ORD gates play a larger role. Plus there are so many segment fliers on ORD-DTW that there will be a lot of competition in both directions on both routes.