SMA PLT UNABLE TO CONTACT FSS OR TRACON FOR IFR CLRNC; MISJUDGED WX CONDITIONS; DEPARTED VFR AND ENCOUNTERED IMC.

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I HAD AN IFR FLT PLAN ON FILE FROM ZZZ. HOWEVER; I WAS UNABLE TO OPEN IT AND OBTAIN A DEP CLRNC/BLOCKOUT TIME DESPITE NUMEROUS ATTEMPTS TO REACH FSS WHILE ON THE GND. THESE ATTEMPTS INCLUDED THE FOLLOWING: 1) ATTEMPTED TO CALL TRACON ON FREQ -- TRIED AT MULTIPLE POS WHILE TAXIING TO RWY NO RESPONSES. 2) CALLED A NUMBER GIVEN TO ME PREVIOUSLY BY FSS -- NO RESPONSE. 3) CALLED ANOTHER NUMBER GIVEN TO ME PREVIOUSLY BY FSS -- NO RESPONSE. 4) CALLED A 3RD NUMBER; AFTER APPROX 30 MINS ON HOLD I REACHED FSS ON THE OPPOSITE COAST AND WAS TOLD THAT HE COULD NOT HELP ME. HE GAVE ME 2 OTHER NUMBERS TO CALL. FYI -- HE OPENLY VOICED HIS DISSATISFACTION WITH THE CURRENT FSS SYS. 5) CALLED BOTH THESE NUMBERS; THERE WAS NO RESPONSE AT ONE AND THE OTHER WAS 'REMOVED FROM SVC.' THE TIME WAS NOW APPROX XA30 AND THE CEILING APPEARED TO BE LIFTING FROM THE EARLIER RPTED 700 FT AT ZZZ1 (ZZZ HAS NO RPTING SVCS). I MADE A DECISION TO DEPART ASSUMING THE CEILING WAS NOW VFR; WOULD LOOK FOR IMPROVING CONDITIONS TO THE E AND WOULD ALSO CONTACT TRACON TO OPEN MY IFR FLT PLAN. THE ACFT IS EQUIPPED WITH TFC AND TERRAIN AVOIDANCE. I MONITORED BOTH LCL AND APCH FOR ANY NEARBY TFC (NO ACTIVITY HEARD IN THE AREA). ALSO THERE WAS NOT ANY TFC BEING PAINTED IN A 10 MI RADIUS. SO; I DEPARTED RWY TO THE S. HOWEVER; THE CEILING WAS LOWER THAN ANTICIPATED AND I ENTERED THE CLOUDS BELOW 1000 FT AGL. HOWEVER I QUICKLY BROKE OUT A FEW SECONDS LATER AND FLEW VFR TO THE ZZZ2 AREA. MY MISTAKE WAS ENTERING IMC CONDITIONS WITHOUT A CLRNC. I RELIED ON MY ACFT EQUIP; HOWEVER I COULD HAVE HAD AN EQUIP FAILURE OR ENCOUNTERED TFC WITHOUT A XPONDER. SO MY LESSONS LEARNED INCLUDE: 1) REPOSITION THE PLANE TO ANOTHER ARPT THE NIGHT BEFORE AN IFR FLT. 2) CANCEL/RESCHEDULE A BUSINESS MEETING RATHER THAN RISKING THE FARM. 3) DETERMINE ANOTHER WAY TO SUCCESSFULLY REACH FSS FROM ZZZ.