How should I approach this in SQL Server 2005?
Also, what kind of problems should I expect while doing an in-place upgrade, especially in the context of converting or upgrading logins?
In SQL Server 2005, objects are no longer qualified by owner. Instead, they're qualified by schema name. This is something I covered in a recent SearchSQLServer.com tip on SQL Server 2005 permissions. In essence, this will result in less confusion regarding object qualification; you will be able to organize objects logically, rather than by who owns them.
As for server logins, I don't see a lot of potential issues. The same semantics apply in terms of what logins are to SQL Server and how they work. One difference you might want to be aware of is SQL Server 2005's ability to enforce password policies, which may mean that some of your users will have to change their passwords after your upgrade.
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