DSM-MKE is 311 miles
I've flown MKE-STL (317 miles) a few times in the Beech. With high winds slowing things down and forcing circling the airport, my longest flight was over 2 hours wheels up to wheels down. A long time in a cramped plane with no lav or service!
I do know that the B1900 often shuttle fuel. Basically they fill up once in MKE and then do the round-trip without refueling at the outstation. While it's more expensive to carry the extra weight on the outbound, it saves money by not having to contract fuel at each little airport.
Once on a GRR-MKE leg we were about to depart when the pilot announced we were going to take on fuel in GRR, something they normally didn't do, due to high winds on the way there.
If anyone here knows; I would love to know what the fuel burn rate is for the B1900, and at what level the pilot would have mentioned his fuel level to the tower to get priority landing.