ACFT RADIO EQUIP PROB IN OVER-WATER FLT IN SMA TWIN.

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ON SEVERAL PREVIOUS FLTS IN THE ACFT INTERMITTENT RADIO XMIT PROBS WERE RPTED. THESE OCCURRENCES CAUSED A MAINT ACTION TO REPAIR WHAT APPEARED A BROKEN WIRE NEAR AUDIO PANEL. INITIAL FLT AFTER REPAIR WAS UNEVENTFUL UNTIL A HDOF FROM ACY TO NY APCH WHILE PROCEEDING ENRTE AT 7000 FT MSL AND ON V139. XMIT COMS FAILED WHEN ATTEMPTING TO ACKNOWLEDGE ACY HDOF FREQ. AFTER TRYING SEVERAL COM CONFIGNS WITH NO SUCCESS I SQUAWKED 7600 AND PROCEEDED ON THE LAST CLRED FLT PLAN -- HARBO V139 RICED MAD RADIAL 193 DEGS KEYED DIRECT. BECAUSE OF THE DISTANCE FROM ACY; I WAS UNABLE TO RECONTACT ACY ONCE I SET UP MY HANDHELD TRANSCEIVER FOR OP. I THEN ATTEMPTED TO CONTACT NEW YORK APCH; BUT DUE TO 'FRINGE' AREA AND 30 MI 'AT SEA' POS; MY LOWER PWR HANDHELD WAS UNABLE TO BE RECEIVED. I CONSIDERED TRANSMITTING ON 121.5 HOWEVER I DID NOT SEE THE SIT AS AN EMERGENCY AND DECIDED TO SAVE MY HANDHELD'S PWR TILL CLOSER TO SHORE (20-25 MINS) AND CONTINUE TO MONITOR NEW YORK APCH AS I HAD NOT LOST THE RECEIVE COM ON MY MAIN RADIOS. WHEN I WAS 5 MI FROM RICED I ATTEMPTED AGAIN TO CONTACT NEW YORK AND THIS TIME WAS SUCCESSFUL. I RETURNED TO MY ORIGINAL SQUAWK CODE AND NEW YORK AND BOSTON APCH HELPED ME MINIMIZE MY XMISSIONS. MY DEP ON EMER LOSS OF COMS PROCS IN THIS CASE WAS VITAL; HOWEVER THERE WERE 2 ITEMS THAT MAY HAVE CONTRIBUTED TO MY DILEMMA AND EMER WORKLOAD; BEING SINGLE PLT. FIRSTLY; DUE TO THE FACT THAT I HAVE 2 IDENTICAL MINIPLUGS ON MY PANEL; NEITHER WHICH IS MARKED; I INITIALLY PLUGGED MY HANDHELD EXTERNAL ANTENNA PLUG INTO THE AUDIO (WRONG) JACK. ALTHOUGH IT TOOK ME 1-2 MINS TO FIGURE OUT THIS MISTAKE I LOST VALUABLE TIME AS I WAS NOW 6 MI FURTHER FROM SHORE AND HAD USED VALUABLE BATTERY PWR FROM MY HANDHELD. SECONDLY; THE RTING I WAS GIVEN (OVER 30 MI FROM SHORE) V139 WAS NOT WHAT I REQUESTED IN MY FLT PLAN; AND IS INAPPROPRIATE FOR SOME LIGHT ACFT DUE TO EQUIP AND CREW SITS. NEEDLESS TO SAY I AM PLACARDING MY 2 MINI- JACKS PRIOR TO NEXT FLT BUT I BELIEVE AN ALTERNATE ATC PREFERRED RTE SHOULD BE PROVIDED TO THOSE PLTS WHOSE CONDITIONS WARRANT OVER-LAND RTING.