VINTAGE ACFT CHKOUT. IMPROPER GEAR INDICATION; LNDG WITH PARTIALLY EXTENDED GEAR.

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I WAS IN THE PROCESS OF BEING CHKED OUT IN A 194X BIPLANE AT WILSON; NC; ARPT (W03). I WAS FLYING WITH THE OWNER; MR. X; AND WE WERE DOING TOUCH AND GOES ON RWY 3. WE HAD MADE SEVERAL LNDGS WITHOUT ANY ABNORMALITIES. EACH TIME THE GEAR (ELECTRIC) WAS SELECTED TO THE DOWN POS THE GREEN LIGHT INDICATING 'DOWN AND LOCKED' CAME ON AND I CALLED OUT 'WE'VE GOT A GREEN LIGHT'; AND HE WOULD CONFIRM IT. ON THE THIRD OR FOURTH LNDG WE FOLLOWED THE SAME PROC WITH THE GEAR AND WE INDEED HAD A GREEN LIGHT. UPON TOUCHDOWN; I FELT A VIBRATION IN THE GEAR AND HEARD A SLIGHT SCRAPING NOISE SO I IMMEDIATELY ADDED PWR AND LIFTED OFF AGAIN. ONCE AIRBORNE; WE SELECTED 'GEAR UP' AND THE RED INTRANSIT; OR WARNING LIGHT; STAYED ON AS WELL AS THE GREEN; SAFE; LIGHT. WE CONCLUDED THAT THE GEAR DID NOT RETRACT FULLY BY THE LIGHT INDICATIONS AS WELL AS AIRSPD AND NOISE INDICATIONS. AT THAT TIME; WE DECIDED TO RETURN TO RALEIGH-DURHAM (RDU); WHERE THE ACFT IS BASED. WE DID ATTEMPT A MANUAL RETRACTION; BUT TO NO AVAIL. BECAUSE MR. X HAD MORE TIME IN THE AIRPLANE THAN I; WE SWITCHED SEATS BEFORE REACHING RDU; JUST IN CASE SOMETHING WAS WRONG WITH THE GEAR. AT THE APPROPRIATE TIME ON THE VISUAL APCH TO RWY 32; HE SELECTED 'GEAR DOWN' AND THE GREEN LIGHT DID ILLUMINATE INDICATING THE GEAR WAS DOWN AND LOCKED. HE DID ENGAGE THE HAND CRANK TO MAKE SURE THE GEAR WAS LOCKED; AND DUE TO THE FACT THAT THE CRANK WOULD NOT TURN ANY FURTHER; HE WAS SATISFIED THAT THE GEAR WAS DOWN AND LOCKED. TOUCHDOWN WAS NORMAL. UPON ROLLOUT THE R BRAKE FAILED AND THE AIRPLANE VEERED SLOWLY OFF THE RWY INTO THE GRASS ON THE L SIDE OF THE RWY. WE NOTIFIED THE TWR OF THE BRAKE SITUATION. MR. X WAS ABLE TO TAXI THE AIRPLANE BACK ONTO THE RWY; CROSS IT; AND STOP ON THE TAXIWAY ON THE R SIDE OF THE RWY. WE ASKED THE TWR TO SEND A CFR TRUCK TO COME OUT AND PICK US UP SO THAT WE COULD GO TO OUR HANGAR AND GET OUT THE ACFT TUG AND TOW THE ACFT BACK TO OUR HANGAR FACILITY. MR. X SHUT THE AIRPLANE DOWN AND WE BOTH EXITED THE ACFT. UPON FIRST GLANCE AT THE FRONT OF THE ACFT; WE NOTICED THE PROP TIPS WERE CURLED AND BRAKE FLUID WAS RUNNING OUT OF THE R BRAKE ASSEMBLY. AFTER CLOSER EXAMINATION; WE NOTICED THAT THE BRAKE HOUSINGS ON BOTH MAIN WHEELS HAD BEEN GND DOWN AND THE OUTSIDE SECTION OF THE GEAR DOOR FLAPS HAD BEEN GND AS WELL. THE R BRAKE WAS LEAKING FROM THE GND PORTION ON THE SIDE OF THE BRAKE ASSEMBLY. AT THIS TIME; WE PIECED TOGETHER THE EVENTS AND CONCLUDED THAT THE GEAR HAD NOT BEEN DOWN AND LOCKED AS THE LIGHT INDICATED; IT HAD ONLY BEEN PARTIALLY DOWN. AS A RESULT OF THE UNLOCKED GEAR; THE PROP MUST HAVE STRUCK THE RWY DUE TO THE ACFT'S SLIGHTLY LOWER ATTITUDE. NOT UNTIL WE CAN HAVE OUR MECH PUT THE ACFT ON JACKS AND CONDUCT SOME TESTS WILL WE BE ABLE TO DETERMINE WHY WE HAD A GREEN LIGHT WHEN; IN FACT; THE GEAR WAS NOT LOCKED IN THE DOWN POS ON THE LAST ATTEMPTED LNDG AT W03. A STUCK SQUAT SWITCH; STUCK IN THE GREEN OR 'DOWN AND LOCKED' POS COULD BE THE REASON FOR THE ERRONEOUS LIGHT INDICATION.