I went through this once upon a time:
http://community.dynamics.com/product/crm/crmtechnical/b/crminogic/archive/2011/01/04/crm-4-to-crm-2011-upgrade.aspx
I recently did an Inplace Upgrade, but that is because of lack of resources, if it wasnt for that, I would go for full crm install then do an upgrade via importing organization db:
Please make sure you login to the server with an account that has access to the crm 4.0 you are attempting to upgrade and:
Sandbox Service runs under an account that has access to CRM - this service imports all your plugins to the new crm 2011
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