I had faced some issues in DBmail configuring , try checking the SSL this helped me once(Check button).

Even i had faced the same issue but user was a database owner in my case, so i tried like

changing EXEC Sp_changedbowner 'SA' and tried dropping the user...

Normally , on PRD box its not required to install reporting services unless required, but we use ssis for many data pulls,maintenance plan so SSIS is ok.

Hope You can use generate script wizard and script whole database objects,data and select the older version(SQL 2008) and create a new database on SQL 2008.(this is the only way...

You require SQL Native client or Microsoft oledn provide for SQl .

Need oracle client to be istalled on server you need to connect for oracle .

you can use OLEDB connection...