The latest OctoPi release with the latest OctoPrint already included and OctoDash pre-installed.
This repository automatically updates the OctoPrint installation on the latest OctoPi image and provides the resulting image ready to flash. Checkout the releases.
A simple update script is run via CustoPiZer.
All that is done is running the equivalent of pip install -U OctoPrint==<latest version>
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Sure, check out CustoPiZer's README for instructions on how to set up your own image build for modified but clean OctoPi images!
That's the plan, but that first requires this automation to get some more testing. It's been wired up into OctoPrint's release workflow now, so next OctoPrint release should show if it that triggers a build correctly. If that works, some further automation needs to be written to automatically update the web page with a link to the latest image and also generate a release file for the imager.
Nowhere, because this really is just a build automation.
If you need support with OctoPrint or OctoPi, please get in touch on the OctoPrint Community Forums.