MLG CAPT INPUTS OM INFO INSTEAD OF VOR INTO FMC. NAV ERROR RESULTS. FLC QUALIFICATION PROFICIENCY IN DOUBT.

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BACKGND: THIS IS 2ND INCIDENT OCCURRING ON A 3 DAY TRIP - - CAPT WAS NEW TO THIS 'HIGH TECH' 737-300 AS WELL AS NEWLY UPGRADED. I HAD SPENT THE PAST 1/2 HR SHOWING HIM SOME WAYS OF USING THE FMC NAV SYS; WHICH HE WAS NOT VERY FAMILIAR WITH. APCH GAVE US DIRECT TO THE LOUISVILLE (IIU) VOR. HE SELECTED THE OM; NOT THE 002 IN THE CDM. BOTH WERE FAIRLY CLOSE; AND AT OUR DISTANCE (80 MI). THERE WAS HARDLY ANY DIFFERENCE IN THE HDG. I ASSUMED HE INTENDED TO ASK FOR DIRECT TO THE OM OR CALL THE FIELD IN SIGHT AS WE GOT CLOSER; AND MADE THE COMMENT 'I GUESS IT'S CLOSE ENOUGH FOR GOV WORK.' HOWEVER THIS MILD SARCASM WENT OVER HIS HEAD. I HAVE IN THE PAST SEEN CAPTS DO THIS (CLRED FROM LAX DIRECT EWR AT MIDNIGHT). THEY PUT IN THE OM; ETC. I DON'T APPROVE OF IT; BUT SOMETIMES ONE GETS TIRED OF NIT-PICKING THE CAPT. ALSO; THIS WAS A FATIGUING PAIRING; LATE FLYING; XING TIME ZONES; ETC; AND I WAS GETTING MENTALLY FATIGUED TRYING TO KEEP UP WITH THIS GUY'S NUMEROUS PROCEDURAL MISTAKES. ATC ASKED IF WE WERE PROCEEDING TO THE VOR. I ASKED THE CAPT WHAT RESPONSE HE WANTED ME TO GIVE OR DID HE WANT ME TO ASK FOR A VISUAL. FINALLY HE REALIZED HIS MISTAKE AND HAD ME ASK FOR A VISUAL. THE ARPT; KSDF; WAS NOT IN OUR FMC DATABASE AND I HAD TO 'BUILD IT' FOR HIM (HE DIDN'T KNOW HOW) -- THEN GOT IN A LONG INFLT DISCUSSION OF HOW TO BUILD THE OM USING A RADIAL AND DISTANCE FROM IIU. THIS IS INFO A CHK AIRMAN SHOULD HAVE COVERED WITH HIM DURING IOE.