MSN CTLR ACTIONS NOT TIMELY TO SEPARATE OVERTAKING TFC AT 6000 FT.

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RADAR SECTORS COMBINED. TFC DENSITY (10+ ACFT) CONTRIBUTING TO SINGLE CTLR SATURATION. NO ASSOCIATE OR HDOF POS FOR THIS OR ANY RADAR POS AT THE TRACON. ATC SPECIALIST AT MSN ARE NOT TRAINED FOR; AS WELL AS; NOT PROFICIENT TO WORK THIS VOLUME OF TFC. MGMNT INABILITY TO DESIGN/DEVELOP POS (IE; HDOFS OR ASSOCIATE) ABLE TO RELIEVE WORKLOAD ON RADAR CTLR WITH REGARDS TO COORD; STRIP MGMNT; FLOW CTL; ETC. A RADAR SECTOR IS CREATED FOR 7-10 DAYS OF EAA CONTRIBUTING TO AIRSPACE STRATIFICATION. THIS POS IS NOT STAFFED OR DECOMBINED FOR THE 355 DAYS PRECEDING EAA. FREQ CONGESTION RELATED TO EAA ACFT REQUESTING SVCS -- BOTH IFR AND VFR. ZAU; AS WELL AS MSN ATCT; WORKLOADS ARE SO DEMANDING THAT MANUAL (VERBAL) COORD; WITH REGARD TO HDOFS; WAS REQUIRED BY MYSELF ON 2 JET DEPS AT THE TIME OF THE OPERROR. NORMALLY; AUTOMATION SATISFIES THIS REQUIREMENT. 4 LANDLINE (VERBAL) CALLS WERE MADE REGARDING THE 2 JETS. HAD THE CALLS NOT OCCURRED; 2 ADDITIONAL OPERRORS OR DEVS MAY HAVE. INSUFFICIENT STAFFING DUE TO FAA DOWNSIZING POSES THREATS AGAINST DEVELOPMENT OF MUCH NEEDED ASSOCIATE AND HDOF POS REQUIRED TO PRECLUDE FURTHER OPERRORS/OPDEVS. LAHSO WAS A MAJOR CONTRIBUTING FACTOR. MSN RWYS ALL INTERSECT. PRIOR TO ALPA/FAA NEGOTIATIONS OF LAHSO; TFC FLOWED ROUTINELY WITHOUT DELAYS. ACR AIR CREW REFUSAL TO ACCEPT A GA ACFT TO HOLD SHORT OF THE ACR RWY HAS EXTREMELY INCREASED WORKLOADS AND VECTORS. IN THIS SIT; HAD THE ACR AIR CREW BEEN ABLE TO ACCEPT THIS CLRNC; THERE WOULD NOT HAVE BEEN A VECTOR THAT CONTRIBUTED TO THE OPERROR. THE ARTS IIE EQUIP FAILED TO ALERT MYSELF TO A POTENTIAL CONFLICT. THE ACFT CONCERNED WERE ON A COLLISION COURSE AT 6000 FT; 1 3/4 NM APART AT THE CLOSEST POINT OF APCH WHEN I OBSERVED THE ACFT AND TOOK IMMEDIATE ACTION. ARTS IIE EQUIP IS ROUTINELY UNRELIABLE IN PROVIDING CTLRS WITH ALERTS IN A TIMELY MANNER; THEREFORE SACRIFICING SEPARATION.