VERY dry market, both corporate and 135. Aviation Charter Services at IND requires Wyvern minimums. He can always go knock on the door at the local airports (TYQ, UMP, EYE, MQJ) and see what opportunities are out there. Also some of the regional airports (BAK, LAF, MIE, AID, FKR, OKK, etc) might have some charter or small corporate operators that I am not aware of.
I'd suggest Republic Airways with those times, or him driving 100 miles south to Louisville...its a much better market with more opportunities IMO.