ObLRPD: Considering that all you're risking is the $15 co-payment, there's no harm in giving him a shot at it.

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I understand and largely share your thinking on migrations. Fell-swoop is hard to go.

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I'd attack the gradualism premise on two fronts:

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  • Replace MSFT server apps with corresponding free software alternatives. For calendaring, take a look at [link|http://otn.oracle.com/products/cs/content.html|Oracle's Collaboration Suite]. It's web and server based, with very aggressive pricing, and some pretty strong recommendations. See also the TWIT [link|http://twiki.iwethey.org/Main/ApplicationsCalendaring|Calendaring page].
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  • Desktop apps. Sounds like you're doing this: OpenOffice, Mozilla, and the GIMP are first-run options. There's the [link|http://gnuwin.epfl.ch/en/index.html|GNUWin II] free software apps for Windows disk, which is decent, though something of a mixed bag. Still, transitioning to portable apps, then porting OS, makes the transition smoother.
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