[KevinH]

No auto checkpoints will be added. It is a single click to generate one. Only the user can judge when a full checkpoint is needed. Especially as the DryRun replace all allows you to verify correctness easily before large scale find/replace changes.

Annotated Tags with Tag messages are already being used by Checkpoints. The Tag message is autogenerated to keep things a single click.

So the only question is about prompting for every checkpoint or allow it only after the checkpoint in the manager if the user wants to add a different message.

I do not think prompting for every checkpoint is a good idea. It will just slow things down and is not actually needed. Each annotated tag already has time and date info. The manager will already show that info as well as a summary of files changed by each tag. Detailed compares can be done between any two tags to see specific changes if the file summary is not enough.

So if we decide to add this then I think it should be done by adding a message after the fact by selecting a tag. But I took a look at how that could be done as well.

There is already a gitignored .bookinfo file that keeps track of current repo head status. It could also keep a tag message history since dulwich does not support the git --edit switch on tags to allow updating the message. Using Tag delete and create does not work as the tag is always built from current HEAD which may differ from when the Tag was originally created. We could try manually editing the tag object in the dulwich object store but that will need to be tested to see if it is possible.

So there are problems to be overcome with both suggested approaches if we decide to do this.