Special Oracle Order

I'd suspect some for of characterset conversion issue. When you do a TO_CHAR, you are getting back "┐┐┐┐┐┐┐┐┐┐┐┐┐┐┐┐┐┐" (18 characters). That suggests that there is some confusion about whether the data contained in the column is single-byte or multi-byte.

"The uniqueidentifier data type in SQL Server is stored natively as a 16-byte binary value" This should ideally come across to Oracle as a RAW datatype not a VARCHAR2 or CHAR.

If you do a

CREATE VIEW temp_view as select  "id", "folder_id" from dbo.mediasite_presentation@ms

what shows up when you do a DESC temp_view

SELECT *
FROM Mytable
ORDER BY
   userID, Date

I assume Date is really a date/time type and not varchar...

Edit, after clarification:

Untested

SELECT
    M.*
FROM
    ( --one row for each user
    SELECT MIN(Date) AS FirstUserDate, userID
    FROM MyTable
    GROUP BY userID
    ) foo
    JOIN
    MyTable M ON foo.userID = M.userID
ORDER BY
    foo.FirstUserDate, M.userID, M.Date;