Short: Does anyone have any strategies for negotiating a bump on an oversold flight ~3 hours before getting to the airport where the flight is originating from?

Situation: Tomorrow, my wife and I fly MSY-MEM-MKE. MSY-MEM looks fine. She even got the advance upgrade as a silver. The second flight (MEM-MKE) shows 0 availability in any class on ExpertFlyer. The seatmap shows 12 of 50 seats (CRJ) unassigned with ~36 hours until the flight, all of them premium seating. DL and ITA are not listing this flight for sale. It feels like a good bump opportunity (and I'm getting low on DL vouchers).

Unfortunately, it's the late MEM-MKE flight and if we need to negotiate the bump in MEM, we'll have no DL options (though there is a US option). Since this is a quick trip to see her family, losing a night to a stay in MEM is going to be a difficult trade off and the morning flights don't have great timing.

Anyone have any strategy for negotiating the bump from MSY so we can choose a routing through another hub (ATL, DTW, CVG), probably ~3 hours before the MEM-MKE flight?

I'm pretty sure this isn't possible but the possibility of 2 bumps sounds great to me.

Other strategies:
* I could SDC to an earlier flight so I had more time in MEM to negotiate the bump but the last option out is ~1:30 before my flight so it seems unlikely I could get that bump that early. I'd have to pay for my wife to do this though.
* At MEM, I could insist on voucher + US Air routing. Doubt they'd accept.
* At MEM, I could insist on voucher + hotel + UA routing in morning. Doubtful.
* At MEM, I could insist on MEM-MSP that night, airport hotel in MSP, and 6am flight to MKE in the morning. That timing wouldn't be too bad for the vouchers.

Hmph. If it were me, I'd have no problem getting creative. But I'd like to prepare my wife a bit. She's said there's no question that we do the bump if we can get in the same night but I'm not feeling like it's possible.

Thanks for any advice! Might all be for naught but it's fun to turn over in my mind.