PLT OF A MOONEY M20J FLEW INTO CLOUDS AT 500 FT AGL DURING A VFR DEP FROM OSH.

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AT ABOUT XA30; I CALLED FLT SVC FOR A WX BRIEFING FROM OSH TO TRI. THEY RPTED IFR CONDITIONS AT OSH WITH CLOUD TOPS AT ABOUT 4000 FT MSL. I FILED AN IFR FLT PLAN TO DEPART AT XB30. I CONTACTED OSH CLRNC DELIVERY FOR A DEP CLRNC AND WAS INFORMED THAT I WAS ABOUT #50 IN LINE. I MONITORED THAT FREQ ON A HANDHELD RADIO FOR ABOUT 2 HRS DURING WHICH TIME LESS THAN 10 IFR AIRPLANES WERE CLRED FOR FLT. AT ABOUT XC30 IT WAS ANNOUNCED OVER THE CLRNC DELIVERY FREQ THAT OSH WAS VFR (CEILING 1100 FT; VISIBILITY 3 MI) AND THAT ANYONE WISHING TO DEPART VFR COULD PICK UP THEIR IFR CLRNC UPON REACHING 9000 FT. I DISCUSSED THE WX SIT WITH A CREW WHO HAD JUST LANDED AND THEY FELT THAT I COULD SAFELY DEPART VFR; STAY UNDER THE CEILING; PROCEED TO LAKE MICHIGAN AND HEAD S WHERE CONDITIONS WERE CAVU. THEREFORE; WE DEPARTED RWY 9 AND ENTERED THE CLOUDS AT ABOUT 500 FT AGL ON AN EASTERLY HDG. I FELT THAT CONTINUING TO CLB WAS OUR ONLY SAFE OPTION. WE BROKE OUT OF THE CLOUDS AT 8000 FT MSL; HOWEVER; WE WERE IN AND OUT OF CLOUD LAYERS UP TO 8000 FT. I CONTACTED GREEN BAY APCH AND THEY ACCEPTED WITH IFR. THIS WAS OBVIOUSLY A VERY UNSAFE SIT THAT I FEEL WAS PRECIPITATED BY BAD WX INFO AND LACK OF SYS CAPACITY TO ACCOMMODATE IFR TFC IN THE CHICAGO AREA. INCIDENTALLY; AN ACQUAINTANCE ALSO FLYING A MOONEY THAT DAY IN THESE CONDITIONS HAD AN NMAC WITH 2 TWINS.