First, you didn't ask for an SSIS solution, you asked for a SQL solution.
Second, use the right tool for the job. This isn't a job for SSIS, it is a job for SQL.
Third, I have another SQL solution:
with TestData as (
select
PassM,
cast(EnterDt as datetime) EnterDt,
ConsecutiveD
from
(values
('Boo K K','5/1/2012 11:55:00 PM', 1),
('Boo K K','5/2/2012 11:30:00 PM', 2),
('Boo K K','5/4/2012 10:30:00 AM', 1),
('LIAW S','4/30/2012 11:48:52 PM', 1),
('LIAW S','5/1/2012 00:11:07 AM', 2),
('LIAW S','5/1/2012 11:59:07 AM', 2),
('LIAW S','5/1/2012 4:42:02 AM', 2),
('LIAW S','5/2/2012 1:10:09 AM', 3),
('LIAW S','5/2/2012 1:43:06 AM', 3),
('LIAW S','5/4/2012 2:17:47 AM', 1)
)dt(PassM, EnterDt, ConsecutiveD)
)
, GrpDates as (
select
PassM,
EnterDt,
GrpDate = dateadd(dd, dense_rank() over (partition by PassM order by dateadd(dd,datediff(dd,0,EnterDt),0)) * -1, dateadd(dd,datediff(dd,0,EnterDt),0)),
ConsecutiveD
from
TestData
)
select
PassM,
EnterDt,
ConsecutiveD,
dr = dense_rank() over (partition by PassM, GrpDate order by dateadd(dd,datediff(dd,0,EnterDt),0))
from
GrpDates
order by
PassM,
EnterDt;
When you run the code above, compare the ConsecutiveD column (the expected results) to the dr column (the computed Consecutive Days column).