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If you can afford to do it the way you suggest it can certainly be a lower risk option than upgrading especially as you say you are a newbie to Notes/Domino.
However if you are going to co-exist 5 and 8 I think the Domino Directory is your main issue. Upgrading direct from 6.5 to 8 is supported (and hence the scenario where 6.5 servers have an R8 DD) but 5 to 8 is not officially supported. So if you plan to have a 5 server and an 8 server in the same domain you may hit issues with an R8 design DD on a 5 server.
You could suppress the design replication of the DD but you may also get other co-existence issues.
Feedback response number WEBB7FCG5S created by ~Gus Loplubergoopsi on 06/06/2008