Roosevelt is an absolute dumpster fire of a place to play football. I don't see anyway they ever have a respectable Division 2 program.
Their campus is a high rise in downtown Chicago and their football facility is in Arlington Heights. That's a 24mile drive to practice down interstate 90. The team takes buses to and from practice each day.
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Morris Field to Roosevelt University
Since the cafeteria is closed by the time the guys get back from practice, the team is given fast food for the bus ride home from practice each day.
The coach they had for the past 10-15 years just left for a D3 job.
They won't ever get enough talent to compete against the schools in their conference. They will get D3 talent that is drawn to the allure of a scholarship but they won't get actual high caliber D2 talent.
They will always have attrition issues because of the logistical nightmare the football program is set up with.