A CL65 FLT CREW WITH A DEFERRED FMS IS UNABLE TO MEET AN ASSIGNED XING RESTR.

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HAD BEEN RE-QUALIFIED ON THE AIRPLANE INCLUDING FMS FOR NAV; HOWEVER; THE ACFT ON THIS FLT HAD THE FMS DEFERRED. WE WERE NAVING USING VOR RAW DATA; SOMETHING OF A CHALLENGE IN ITSELF; MADE EVEN MORE SO GIVEN THE RECENT RETURN TO FLYING AFTER SUCH A LONG LAYOFF. ON THIS FLT FROM XXX TO MEW AT FL230; WE HAD BEEN ON AN OFF-COURSE VECTOR WHEN CTR CLRED US DIRECT CGT; CROSS 45 MI SE OF CGT AT 1000 FT. AFTER I GOT SET UP TO GO DIRECT; IT TOOK ME A MIN TO FIGURE WHAT IT WOULD TAKE TO MAKE THE XING AND I REALIZED THAT I NEEDED TO START DOWN IMMEDIATELY! TRYING OUR BEST AT 3500-4000 FPM DSCNT; I COULD SEE WE WEREN'T GOING TO MAKE THE RESTR; AND TOLD ATC AT 63 DME FROM CGT; ABOUT 8 MI PRIOR TO THE XING POINT; THAT WE WOULD BE UNABLE TO MAKE THE XING. ALL THE CTLR DID WAS HAND US OFF TO ANOTHER CTLR; WITHOUT ANY OTHER RESPONSE OR AMENDED CLRNC; SUCH AS 'DO THE BEST YOU CAN;' OR 'TURN R 30 DEGS;' ETC. NO APPARENT TFC CONFLICT OCCURRED. AT THE SPECIFIED XING POINT; WE WERE DSNDING THROUGH 14000 FT; ABOUT 3000 FT HIGH. I THINK THE REAL CAUSE OF THIS ERROR WAS A LACK OF SITUATIONAL AWARENESS; DUE TO MY LACK OF RECENT EXPERIENCE IN NAVING SOLELY WITH VOR RAW DATA; WITHOUT THE USEFUL VNAV FEATURES OF THE FMS TO HELP WITH DSCNT MGMNT. CONTRIBUTING TO THE ERROR WAS ATC'S RATHER LATE TIMING OF AN UNPUBLISHED XING CLRNC; SOMETHING THAT I WOULD NOT HAVE ACCEPTED IN THE FIRST PLACE HAD I REALIZED HOW TIGHT IT WOULD BE TO MAKE THE RESTR. SINCE WE HAD BEEN TRANSITIONING TO THE BOILER 2 ARR TO MDW PRIOR TO THE OFF-COURSE VECTOR; WE PLANNED FOR THE PUBLISHED XING AT CGT; AND WERE CAUGHT SOMEWHAT OFF GUARD BY THE CTLR'S RAPID-FIRE UNPUBLISHED CLRNC. WE GET SO USED TO HAVING THE ADVISORY VNAV INFO FROM THE FMS ON EVERY FLT; THAT IN RARE CASES WHEN IT'S NOT AVAILABLE; IT CAN MAKE FOR A HIGHER WORKLOAD IF OPERATING INTO/OUT OF BUSIER; FASTER PACED ARPTS/AIR TFC REGIONS. WE HAVE TO BE BETTER PREPARED; THINKING FARTHER AHEAD; TO MAINTAIN BETTER SITUATIONAL AWARENESS SO AS NOT TO BE CAUGHT OFF GUARD.