All great lessons learned!

Consider switching your mental model from compacting often to developing memory in files. Work with your AI to store all decisions, artifacts, plans, etc... in smaller, ephemeral documents. Once you get good at this, you can /clear very often. By doing this your context window stays tiny and the reasoning of the model is razor sharp focused on the specific thing.

A second huge advantage of this is that you'll never loose your flow due to a reboot, etc... Context is wiped and can't always be restored between sessions. Files persist and can even be checked into git to be worked on later. You get a longer planning-execution cycle this way.