Need more info esox! Are you guys serious fisherman or wanting a guys weekend? Are you needing a guide or will you free lance.
How much gear do you have vs. need.
I would go either early or late ice. Reports I hear from LOW in dead of winter are hit or miss, maybe 1 good day on a three day trip.
LOW has much more sophisticated transportation system to get guys to hot fishing spots. DL is a fantastic fishery and has great walleye fishing, but is known for its perch. DL also has a great big pike population.
If you are free lancing either place, be sure to have the gear to do so (sleds, portable towables, etc).
I think it would be a toss up to me and I would end up going where you think you are getting the best deal, accomodations, etc.
ET