I agree that your expected results are wrong because you have an enddate greater than the startdate and that will generate a problem in the next row (rows 3 & 4).

This might give you an idea of what you need to solve your problem, even if I don't understand your "First Date" parameter.

WITH CTE AS(

SELECT *,

ROW_NUMBER() OVER( PARTITION BY id, YEAR(StartDate) ORDER BY startdate) rn,

YEAR(StartDate) DateYear

FROM #table

)

SELECT c1.id,

c1.cid,

c1.startdate,

ISNULL( c2.startdate - 1, CASE WHEN DATEADD(YEAR, DATEDIFF(YEAR, 0, c1.startdate) + 1, 0) < GETDATE()

THEN DATEADD(YEAR, DATEDIFF(YEAR, 0, c1.startdate) + 1, 0) END)

FROM CTE c1

LEFT

JOIN CTE c2 ON c1.DateYear = c2.DateYear

AND c1.id = c2.id

AND c1.rn = c2.rn - 1

ORDER BY c1.id, c1.startdate DESC

EDIT: Code Formatting.