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If you only have a few apps and can upgrade a test server first, then I think I direct upgrade is reasonable in an application-only environment.
In particular, you'll want to decide at what point you want to upgrade your system databases (names.nsf, admin4.nsf) and the Administration Server. Generally, both of these happen early in the upgrade and normally, there's no problem replicating later versions of these templates to older servers. But keep in mind that Lotus will only have tested replicating these designs to Domino 6.5 and 7 servers, so they won't support you if you hit the skids. You may want to have a roll-back plan in case your Domino 5 servers don't like the new designs.
I don't recommend keeping the old versions of these databases on your Domino 8 server, as you're not really testing a proper Domino 8 environment. A third option is to upgrade the design on the test server, but prevent it replicating to the rest of the domain.
Be sure to think through the hardware and OS issues, too, as there's not much overlap between R5 and ND8 specifications for these. That can make both the upgrade and roll-back paths difficult (unless you're buying all new servers).
To ease your worries a little, I can tell you that I am in the process of doing a Domino R5->8 upgrade very much as you describe, and we have hit no major issues so far, though it did help us identify a few areas that needed recoding before upgrading production.
Rupert Clayton
Chicago
Feedback response number WEBB7M7VYG created by ~Anita Asafreezenoopsi on 12/10/2008
It's do-able
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. . It's do-able (~Anita Asafreez... 10.Dec.08) 
