I'll give these a shot - although this is just from what I gathered with a bit of speculation mixed in.
A few things are preventing me from getting excited:
- are they planning edition 5.5 already? I hate half editions.
As I see it, the online document--Basic D&D--will be the core rules of the game, always free and updated with any rules tweaks and additions. The Starter Set will be simple enough to essentially be an evergreen product, so coupled with Basic D&D you can play 5E indefinitely for very little (or nothing if you go by Basic D&D alone).
As for the PHB, DMG, and MM, my guess is that they will revise and reprint them every few years to reflect rules additions, tweaks, etc. Or maybe only the PHB. My guess is that it won't be "5.5" but more like "5.2" in 2-3 years, "5.4" in another 2-3 years, etc.
So rather than saying they're "planning 5.5 already," my sense is that they are trying to make room for inevitable rules tweaks and adjustments, which will always be reflected in the free Basic D&D document. I mean, we
want them to continue to improve the game, right? I think they may have stumbled upon the best way to do that without pissing people off with a major revision every few years - they're offering a high quality PDF for free that will always be up-to-date.
- is this digital toolset thing going to discourage homebrew content, even a little bit?
I don't know how it would, especially when one of the key design goals fo 5E was to make it customizable for individual DMs and groups. If anything they may err on the side of too much homebrew encouragement and leave newbies and RAWists out in the cold a bit. But even that it seems like they're trying accommodate.
Remember also that the DMG is going to be essentially a toolbox for customization, so homebrewing is considered the norm.
Now how this dovetails with the digital toolset, I'm not sure. I'd hope that they have an option to add homebrew options. Given what we've seen so far I'd be surprised if they didn't.
- how is this community marketplace thing going to work? it would be awesome if everything were free to access but WotC gave micropayments to the authors based on views/downloads. That would be a nice compromise between the OGL vanity publishing glut and the slave labor of videogame modding communities.
- why did Monte Cook leave?
No idea on either one.