LIGHT TWIN TURBOPROP PLT RPTS NIGHT VFR FLT BELOW OVCST AND INABILITY TO MAINTAIN FAR CLOUD SEPARATION AND VISIBILITY STANDARDS.

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RETURNING FROM TRIP; I SHOT THE LOC/DME 28L INTO HWD AND DROPPED MY PAX. HAD A POOR NIGHT'S SLEEP; HAD BEEN ON DUTY FOR 13 HRS AND STILL HAD TO FLY BACK TO PUT THE PLANE AWAY. IT WAS ABOUT XA00; DARK AND OVCST. HWD AND OAK WERE RPTING CEILINGS OF AT LEAST 2000 FT AND VISIBILITIES OF AROUND 10 MI. THIS GAVE ME THE IDEA THAT FLYING BACK VFR WOULD BE PRACTICAL. WAS CLRED FOR TKOF WITH A L OVERHEAD 270 DEG TURN DEP FROM RWY 28L AT HWD. CROSSED THE ARPT; NBOUND; AT 1000 FT AS REQUESTED THEN CLBED TO 1300 FT TO REMAIN UNDER OAK CLASS C. TOOK A WHILE FOR HWD TWR TO HAND ME OFF TO OAK TWR AND WAS HEADING TOWARD RISING TERRAIN SO I INITIATED A 360 DEG TURN TO THE R TO AVOID. JUST THEN WAS GIVEN THE HDOF TO OAKLAND AND TOLD TO REVERSE MY TURN AND HEAD TOWARD OAKLAND'S AIRSPACE. HEADING NW; CLBED UP TO 1500 FT; BUT THE CEILING SEEMED LOWER THAN 2000 FT; SO WENT DOWN TO 1200-1300 FT FOR CLOUD CLRNC AS I PARALLELED THE 880 FREEWAY JUST TO THE N -- MY FIRST MISTAKE SINCE I THOUGHT THAT WAS AS BAD AS IT WOULD GET. AFTER OAK; I PASSED OVER DOWNTOWN OAKLAND. NOT WATCHING THE OVCST TO MY L AND R AS I CHKED MY TCAS AND LOOKED AT THE GND WHILE TRYING TO ENSURE THE MINIMUM 1000 FT SEPARATION FROM THE TALLER BUILDINGS; I EVENTUALLY NOTICED THAT THE CEILING WAS LOWERING SOMEWHAT AHEAD BUT HAD REALLY LOWERED ON BOTH SIDES OF ME AND THUS WAS UNABLE TO REVERSE COURSE WITHOUT FLYING BELOW 1000 FT OR INTO THE CLOUDS. FRUSTRATED AT MY SELF-CREATED PREDICAMENT; I NEVERTHELESS HAD TO MAKE UP MY MIND ON WHAT TO DO -- BY NOW ANYTHING I DID WOULD BE OUTSIDE OF THE VFR CLOUD CLRNC REGS. AND NOW I WAS CERTAIN THE CEILING WAS LESS THAN 500 FT OF CLR ABOVE ME. CONTINUING ON SEEMED THE LESSER OF SEVERAL EVILS. I CHANGED COURSE SLIGHTLY TO FLY CLOSE TO THE SHORELINE WHERE THE CEILING WAS THE HIGHEST. WAS AT 1100 FT IN ORDER TO REMAIN BELOW CEILING BY AS MUCH AS POSSIBLE WHEN I NOTICED LOW SCUD AHEAD BTWN EMERYVILLE AND THE BERKELEY PIER. SINCE TURNING AROUND OFFERED AN EVEN WORSE PROSPECT I CONTINUED; TURNING AS NECESSARY TO KEEP AS MUCH DISTANCE AS POSSIBLE BTWN THE SCUD AND THE PLANE. RIGHT AROUND THE BERKELEY PIER EVERYTHING CHANGED TO COMPLETE VFR AND THAT WAS THAT. THE REST OF THE FLT WAS OK BUT I FELT STUPID FOR GETTING MYSELF INTO A SITUATION WHERE I COULD NOT MAINTAIN VFR CLOUD CLRNC; ESPECIALLY WHILE OVER A CITY. CONTRIBUTING FACTORS: 1) THE FLYING I HAVE BEEN DOING FOR THE LAST 2.5 YRS HAS BEEN VIRTUALLY ALL JET; ALL IFR AND ALL 2-PLT -- EVERYTHING HAD BEEN VERY PREDICTABLE. I WAS IN THIS TYPE OF MINDSET GIVEN THE 2000 FT CEILINGS BEING RPTED -- THOUGHT IT WOULD BE A ROUTINE PIECE OF CAKE. 2) FIRST SINGLE PLT FLT IN A LONG TIME AND IN A PLANE I WAS NOT ACCUSTOMED TO DIVERTED SOME OF MY ATTN. 3) FATIGUE AND JUST WANTING TO GET HOME BROUGHT ABOUT NOT ONLY A LOWER AWARENESS OF MY SURROUNDINGS BUT AN IMPATIENCE THAT CAUSED ME NOT TO PICK UP THE IFR CLRNC FOR THE FLT PLAN I HAD ALREADY FILED. I CAN SEE HOW THIS AFFECTED MY JUDGEMENT THROUGHOUT THE FLT. 4) FORGOT THAT THE FOG IS USUALLY LOWER BTWN WEST OAKLAND AND RICHMOND THAN AT THE OAKLAND ARPT. 5) DID NOT THINK THE CTLR COULD HELP ME IN MY PREDICAMENT BUT PROBABLY COULD HAVE ASKED FOR AND RECEIVED AN IFR TO VFR ON-TOP IF I PROVIDED MY OWN TERRAIN SEPARATION. WAYS TO AVOID REPEATS: 1) FILE AND USE IFR IN MVFR CONDITIONS -- COULD HAVE PLANNED TO SHOOT THE APCH TO GET UNDER THE 2000 FT OVCST BASED ON A 2000 FT CEILING; BUT WOULD HAVE NOT EVEN HAD TO DO THAT SINCE PART OF SAN FRANCISCO BAY AND MOST OF SAN PABLO BAY WAS CLR. 2) FLYING FOR A LIVING; YOU INEVITABLY HAVE TO FLY WHEN LESS THAN 100%. IN SUCH CASES; I USUALLY FLY MORE CONSERVATIVELY AND TAKE IT EASY -- SHOULD HAVE DONE THIS IN THIS CASE. 3) DON'T GET 'SUCKERED' INTO MVFR SITUATIONS -- THE WARNING SIGNS WERE THERE TO BE RECOGNIZED IF I HAD BEEN MORE COGNIZANT -- IT'S JUST NOT WORTH IT. A UNIFORM 1000-1500 FT CEILING DURING THE DAY IN A PIPER CUB IN FLAT FARM-COUNTRY IS ONE THING; THIS WAS ANOTHER.