A PA28 PLT WAS UNABLE TO MAINTAIN CLOUD CLRNC DURING A VFR FLT FROM PAO TO 103.

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THE FLT INVOLVED WAS A 40 MIN FLT BTWN PAO AND 103. AS OFTEN IS THE CASE IN THE BAY AREA; OVCST HAD DEVELOPED OVERNIGHT AND WAS BURNING OFF DURING THE MORNING HRS. 1 HR PRIOR TO OUR SCHEDULED DEP; I CHKED THE RECORDED WX INFO AVAILABLE AT THE OAKLAND AUTOMATED FLT SVC STATION. PAO; SJC; AND HWD WERE ALL RPTING VFR CONDITIONS WITH CEILINGS AROUND 1400-1500 FT. AS WE DROVE TO THE ARPT AND PREFLTED; THE CLOUDS WERE CLRING OVER PAO AND TO THE S WE COULD SEE SUNSHINE OVER SUNOL PASS; WHICH WAS OUR INTENDED RTE OF FLT. THE CEILINGS WERE LOWER FROM HAYWARD TO THE N. WE DEPARTED PAO USING A STANDARD 'R DUMBARTON' DEP AND CONTACTED NORCAL APCH FOR FLT FOLLOWING AND TO ESTABLISH 2-WAY RADIO CONTACT IN THE EVENT THAT OUR FLT PATH TOOK US INTO THE NORTHERN CORNER OF THE SJC CLASS C AIRSPACE. THERE WAS SOME MISCOM WITH ATC AT THIS POINT. RATHER THAN JUST ASK FOR FLT FOLLOWING; I MENTIONED THE CLRNC THROUGH SJC CLASS C. ATC ASKED IF I WAS GOING TO SAN JOSE AND I REPLIED; 'NO; I WAS JUST TRANSITIONING S TOWARD SUNOL PASS TO AVOID THE OVCST.' ATC THEN GRANTED CLRNC INTO CLASS B AIRSPACE; WHICH I NEITHER REQUESTED NOR NEEDED. (IN FACT; THIS WAS NOT POSSIBLE FROM MY LOCATION DUE TO THE OVCST ABOVE. THE CLASS B FLOOR IS 4000 FT IN THIS AREA.) DURING THIS EXCHANGE; ATC NOTED MY MODE C ALT AT 900 FT; AND I REALIZED THAT I HAD BEEN FOCUSED ON MAINTAINING CLOUD CLRNCS ABOVE AND HAD NEGLECTED TO MAINTAIN THE REQUIRED 1000 FT AGL MINIMUM CLRNC OVER THE CITY. I CONFIRMED HIS READING AND CLBED IMMEDIATELY TO CORRECT THE SIT. IN DOING SO I FOUND I WAS UNABLE TO REMAIN 500 FT BELOW THE CLOUDS. I HAD MISJUDGED THE CLOUD LEVEL IN THIS AREA. WITHIN 2-3 MI; THE CEILING LIFTED; I REACHED THE BREAK IN THE OVCST THAT I HAD OBSERVED FROM PAO; AND I WAS ABLE TO CLB ABOVE THE CLOUD LAYER IN VFR CONDITIONS. AT NO TIME WAS MY VISIBILITY LESS THAN 10 MI; BUT AT SOME POINTS I WAS ONLY ABOUT 200-300 FT BELOW THE CLOUDS. THE REST OF OUR FLT WAS UNEVENTFUL. I AM GENERALLY A VERY CONSERVATIVE PLT. MOST OF MY FLYING INVOLVES TRIPS SUCH AS THIS ONE WHERE I AM TRANSPORTING MY FAMILY ON A PLEASURE TRIP. WE USUALLY DO NOT FLY IN ROUGH OR MARGINAL WX. BASED ON 'IFFY RPTS;' I HAVE OFTEN CANCELLED FLTS AND DRIVEN OUR CAR JUST TO AVOID GETTING INTO THE SIT DESCRIBED ABOVE. THIS TIME I BELIEVED THAT THE OVCST HAD CLRED ENOUGH FOR US TO TRANSITION THIS AREA SAFELY WHILE MAINTAINING ALL OF THE APPROPRIATE CLRNCS. BY THE TIME I REALIZED I WAS WRONG; THE SAFEST OPTION WAS TO CONTINUE ON AND CLB OUT. I AM USUALLY VERY ALERT TO 'GET-THERE-ITIS' AND AVOID THAT PITFALL. HOWEVER; IN THIS CASE; I WONDER IF OUR PLANS FOR THE HOLIDAY WEEKEND CAUSED ME TO PUSH MY LIMITS BEYOND WHAT I NORMALLY WOULD HAVE; OR TO MISREAD THE CONDITIONS PRIOR TO DEP? IN RETROSPECT; I REALIZE THAT I SHOULD HAVE DELAYED OUR DEP AT LEAST ANOTHER 1/2 HR TO 1 HR SO THAT THE OVCST WOULD NOT HAVE BEEN AN ISSUE. IT IS ALSO POSSIBLE THAT I COULD HAVE OBTAINED A 'SPECIAL VFR CLRNC' FOR THE TRANSITION; AS VFR UNDER THOSE MINIMUMS WAS EASILY MAINTAINED; BUT THIS DIDN'T OCCUR TO ME SINCE I THOUGHT I WOULD BE OK ANYWAY.