score:-2
I would use the RedGate SQL Compare and SQL Data Compare. That would give you some assurances of the integrity of the database. However its not going to be an online migration of the data, you would have to prevent updates during the transition.
score:1
To transfer logins, you should be able to use the 'Transfer Logins Task' described in Books Online here.
Ross Mistry has published a few articles on SQL Server 2008 Installation Strategies and Best Practices. Also this document, although directed at specific hardware, contains useful info.
EDIT: Have you looked at the Microsoft SQL Server 2008 Upgrade Advisor?
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