Why not save progress and important results of a conversation (i.e. including tool calls and such) to a project markdown (even multiple as needed) and clear your context window completely rather than compacting many times? You can then just specify a markdown file to be included as context. Especially if following any kind of plan document and executing on a part of it.
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It’s the diffrence between net present state and the sequence of events the lead to it, aka event sourcing.
There are pros and cons both ways.
NPS is more succinct and devoid of intermediate deviations, thus less likely to throw the agent off target.
ES otoh does contain deviations which might be salient in the future reasoning. If nothing else then to prune approaches that are known to be dead ends, but also fruitful approaches might have use especially when couple with the line of reasoning that lead to their application.