So for this not to end up too whiny, I decided to actually fix the omnibus_updater issue.
What I got seems to work to some degree in that the MSI gets downloaded and the installation starts. But during the installation it seems like the running chef-client process gets a SIGINT and stops with a failure. But the installation continues (and the RestartManager says a reboot is required)
Recipe: omnibus_updater::downloader←[0m
* remote_file[omnibus_remote[chef-client-11.6.2-1.windows.msi]] action create_if_missing←[0m←[32m
- copy file downloaded from [] into C:/chef/cache/chef-client-11.6.2-1.windows.msi←[0m←[37m
(file sizes exceed 10000000 bytes, diff output suppressed)←[0m
←[0m
Recipe: omnibus_updater::installer←[0m
* ruby_block[Omnibus Chef install notifier] action create←[0m←[32m
- execute the ruby block Omnibus Chef install notifier←[0m
←[0m
* file[/tmp/nocheck] action create←[0m (skipped due to only_if)←[0m
* ruby_block[omnibus chef killer] action nothing←[0m (up to date)←[0m
* windows_package[stfu] action nothing←[0m (up to date)←[0m
* ruby_block[Omnibus Chef install notifier] action nothing←[0m (up to date)←[0m
* windows_package[chef-client] action install←[0m[2014-02-27T22:04:13+01:00] FATAL: SIGINT received, stopping
[2014-02-27T22:04:51+01:00] FATAL: SIGINT received, stopping
================================================================================←[0m
←[31mError executing action `install` on resource 'windows_package[chef-client]'←[0m
================================================================================←[0m
←[0m
SystemExit←[0m
----------←[0m
exit←[0m
After a while the installation does seems to complete...