@Rarst
I think WordPress.org is more concerned about making things as simple as possible for there user base, which mean keeping things consistent both on the WordPress.org site, but also things that are linked to by the WordPress.org site. I see WordPress.org's stance as: "If developers don't like this game, then they should just keep to themselves or find another platform. We have enough developers that are happy with the status que, so we not going to change to make other developers happy at the cost of our community." If WordPress regulates the developers it links to, then each average community member doesn't have to worry about what they are paying for and the restrictions it comes with.
It's probably better for WordPress.org to draw a strict line at first, then relax it if needed, rather than vise versa. I think there are enough happy plugin and theme developers and that making users happy is what they should focus on. Some theme developers are going to try and game the system, so I think it's better to play bad cop, even if some developers who are in the grey get put on the wrong side.
Themes not in the repository can use the automatic upgrade functions in Wordpress if they do a little hacking. It's not hard at all, I've already successful tried. Themes outside of the WordPress.org repository could actually take advantage of the automatic upgrade one version before themes in the repository, if I remember right. Still, it would be nice if API was developed so theme developers wouldn't have to create a-round-about way or make there own automatic upgrade feature.


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