The critical leap here is noticing that you have to “vest” the grant codes by the traditional Microsoft vesting schedule. Note that when multiple letters “vest” in the same period, they all “vest” simultaneously and can therefore be anagrammed.
LASWITLF
TODITFUS
RNOASRJS
EAOHLKNR
MIYAOHSO
ECSOTTRY
7/94: L
1/95: A
7/95: ST
1/96: WO
7/96: RDI
1/97: NTI
7/97: TLEO
1/98: FAFA
7/98: MOUS
1/99: SHIR
7/99: LEYJ
1/00: ACKS
7/00: ONS
1/01: HOR
7/01: TS
1/02: TO
7/02: R
1/03: Y
More compactly, this is LAST WORD IN TITLE OF A FAMOUS SHIRLEY JACKSON SHORT STORY. The answer is LOTTERY.