Here is my 2 cents on what I would do....
WBOW - Oldies (Live AM Drive, track Mid & PM Drive, Mike Harvey at night)
WSDM - Active Rock (No offense to Ed & the crew at the River but it's just kind of there and not very fun or exciting. At least last I listened. Go Mike & Mike in the Morning if they really want, lots of stations have, or grab a Free Beer & Hot Wings or Rick & Bubba type show depending who you want to bring in, Live PM Drive and track the rest)
WAXI - All Sports or AC (Sports put an afternoon person in for a few hours and the rest off ESPN's bird. AC, Bob & Sherri, Live jock, track PM Drive and bring back Delilah at night or Tesh)
WSDX/WBOW AM - News Talk or ALL Sports (See above for sports. N/T, grab Rush and Hannity fill out with WOR programs and Doug Stephans Good Day in AM Drive)
For staff
Get a solid on air talent per station track the rest out of market and syndicate what you can to be as cost effective as possible.
One air talent doubles as Group PD/MD don't let this person do mornings because of their workload
One air talent doubles as Group APD.AMD this person can be a morning host
One air talent doubles as Prod. Director don't let this person do mornings they need to be there through the business day
One air talent doubles as Promo Director this is a sure fire midday person
Then have them all rotate weekends on air and appearances plus toss in 4 or 5 part timers to share between the group for weekends and ball games.
In a different time I would be screaming go live 24/7 but lets face it, that is not the world we live in.