Do you not still see lack of "commodity" hosting as a hurdle? That's always struck me as one of the biggest reasons for first Perl CGI, then especially PHP's rise to ubiquity.
Absolutely; that's part of my plan! Perl CGI was one step; PHP was a different step (notable mod_perl is vaguely similar to mod_php, but the results are much different -- mod_php feels like Perl CGI in important ways). I think the next step will look similar to the app servers we have, but feel like PHP.
I'm guessing the plan is based around paste and wsgi and similar, which seems a good way of handling/building the ecosystem of pluggable apps and so forth, but what do you think about the deployment issue?
I have some ideas, written about here and elsewhere, and I'll try to actually follow through on describing the full plan after Christmas. But yes, deployment definitely matters, and I think there's several tools (most of which exist already) that can work together to make this work well. A lot of them aren't even Python specific. The recent Zope TTW discussions have some important ideas in them as well... the plan shouldn't just be plug-and-play, but plug-play-fiddle-plug-fiddle-play, or something like that. We have to invite users into the development process like PHP (and Zope TTW development) does, but also help teach them about basic development methodology.