Great thread! Sorry it took me a while to post.
Here are my thoughts. I've stolen liberally from Adam's and Antartica's previous posts in making this list.

I have tried to put items in a practical order, so that prerequisites come before advanced steps. I figure things will be moved around if they happen faster or slower than anticipated. I have also tried to put widely-requested UI improvements early, and substantive under-the-hood improvements into later versions.
Versions 2.16-2.19 are sublabeled as "alpha" releases, as most of those changes will be under the hood and will require major testing before a "general public" release. They are also not really fixed in terms of order, I just tried to group related tasks together and keep each version down to a manageable size. We don't want any single version to be so big that it never gets done!
I have probably forgotten to include many major tasks.
What do you think?
First milestone: SVN server contents- "Trunk" : all iRex-released source codes
- "Upstream" : all necessary upstream applications and libraries (i.e. busybox, gtk, kernel, etc.), with versions currently used on the iLiad.
- "Filesystem" : a perfect copy of the current iLiad filesystem, with all libraries, programs, etc. Suitable for distribution.
- SDK?
As new programs and libraries are updated and tested, the newest binaries will be copied into the "filesystem" directory, which will (ideally) always hold a working snapshot that could be installed on an iLiad. The snapshot will be tagged for each version release.
One question: how and where should we maintain the SDK? I do think we should provide a single, simple community SDK, along with clear directions on how to set it up to compile programs, libraries, and the kernel. But I don't know the best way to maintain something like that.
2.13 - Community software- Based on latest iRex release (2.12.1?)
- Include established, proven community software that substantially increases functionality:
- FBReader
- Feedbooks
- Dropbear/SSH
- No iPDF changes yet
- Others?
- Registry updates so all new programs are called to open "their" files types. Associate html files with FBReader. Include sh script support.
- Produce a reflash image of 2.13 suitable for flashing from a CF card.
- Produce a reflash version of iRex 2.12 for reference, and to make it easy for users to revert / uninstall the community OS.
At this point I think we will have established basic development capability.
2.14 - More programs, and community iDS- Introduce Community iDS server
- Add "one-press" upgrade ability to iLiad.
- Add "Programs" folder to ContentLister for running programs not associated with a file type (Sudoku, etc.?). This avoids having to put them in "News".
- Second round of community software additions.
- Introduce automatic conversion/handling of file types (.lit, etc.)
- Simple boot speed improvements via streamlining (if possible).
- Other small, easy improvements not significantly affecting GUI.
- Bugfixes
- Dev Goals
- API Documentation: toolbar, erdm, eripc, etc.
- File formats documented: scribbles, folder manifests, etc.
After manually installing this version, users will be able to get new version updates from the community iDS server instead of the official iRex iDS server. New versions will not be released to the community iDS server until they are beta-tested. Of course, we will also provide new versions as reflash packages. I strongly suggest that we provide a "revert to 2.12" option in the Settings menu of this release.
Bear in mind that no one has worked on how to set up an iDS server as far as I know. If this proves to be difficult, we may have to push back the iDS item, and only release reflash packages for the time being.
2.15 - Major features / UI / GUI release- UI/GUI revisions to toolbar, button functions and menus, according to goals determined in the UI discussion.
- iPDF: add community and new desired functionality (fullscreen, search, etc.).
- Modify other programs (FBReader?) to improve GUI consistency?
- Modify ContentLister to allow multiple documents/programs open at once.
- ContentLister GUI changes to add desired functionality:
- More files visible (6,12,24?)
- Read/unread checkbox, current page info
- Scribble/note box
- Rating in stars
- Allow sorting, searching...
- Etc., see this thread for ideas.
- Settings manager allowing full customization of UI preferences, along with easy "iLiad classic" and "community default" options.
This release is pretty major and will take some time to implement, I think. We will have to break it down into several parallel projects. Much of these are interdependent. For example, changing the toolbar and button UI should be done at the same time as adding iPDF features. The UI change also requires adding a menu to the ContentLister, in addition to new battery functionality.
All of these GUI changes will be planned by consensus. We won't introduce radical changes without vetting and feedback. These versions may go through several alpha/beta/RC steps to gain community approval, before it's released.
2.16 (3.0alpha1) - Infrastructure upgrade- Upgrade all support programs (busybox, etc.) to latest versions.
- Upgrade all libraries (GTK etc.) to latest versions.
- Replace/supplement displaymgr with xepdmgr.
- Update current applications to use the new library; OR
- Include backwards compatibility in xepdmgr.
- Patch/modify major iLiad applications if necessary to handle these upgrades.
- Test, test, test.
2.17 (3.0alpha2) - Kernel upgrade- Upgrade Kernel to 2.6 family.
- Trim unnecessary kernel options (if any) for speed improvements.
- Integrate all kernel modules directly into main kernel for faster boot (if reasonable).
- Obtain new versions of proprietary binary kernel modules for 2.6, or get/implement FOSS replacements.
- Maintain compatibility with applications/libraries.
- NO major changes in kernel functionality (i.e. sleep) in this release.
- Test, test, test.
2.18 (3.0alpha3) - Package-based update system- Add ipkg frontend/GUI for easy selection/removal of community programs/packages.
- Restructure developer SVN server to allow separate maintenance/upgrade of individual packages.
- Revise community iDS to support package-by-package upgrading.
- Test, test, test.
2.19 (3.0alpha4) - Power management: fast boot / sleep / suspend- Using 2.6 kernel, implement some variation of sleep/suspend if possible.
- Streamline boot process even further:
- Revise startup scripts for fastest, most efficient normal boot.
- Provide alternative "minimalist" boot for simple tasks.
- New minimalist applications using smaller libraries for fast startup?
- Test, test, test.
3.0 beta, 3.0 release candidate - Public testing releases- Minor feature additions
- Bugfixes
- Test, test, test.
3.0 - Major version release
This release should be the culmination of the last several milestones, resulting in a fully tested OS that includes most commonly-requested features as well as better libraries and infrastructure supporting future development. With this release iLiad OS can enter a phase similar to other Linux distributions, where individual software packages are maintained and updated independently, with periodic coordinated releases offering the latest feature changes and improvements.
Ongoing projects not specifically listed above:- Add new community software. For inclusion, new software must:
- be thoroughly tested and vetted, free of major bugs;
- add significant useful features;
- provide a smooth and efficient UI designed with e-ink refresh rates in mind.
- Software feature improvements:
- Speed improvements (rendering, page turning, app startup time, etc.)
- Efficient memory usage
- Minor features and UI changes
- Under-the-hood improvements:
- Code cleanup, add comments.
- Write & improve API and general system documentation.
- Split or combine programs for best efficiency and code clarity.
Questions, comments, additions, suggestions, criticism?