Hi @rhigashi, great question!
As you’ve found, often with this type of trigger, the Zap will recognise the change the first time it happens, but the data is changed back to it’s original state, the Zap compares that to the records it as and thinks that it’s seen that value before, so it wont trigger the Zap.
There are two ways to approach working around this: changing the trigger so all information triggers the Zap and you add a filter after the trigger or adding a new field in the HubSpot data and have the Zap trigger from that new field (ie when a deal changes stage, update the new field to a unique value).
In terms of saving tasks in your Zap, the second is the better option. Are you able to create a field in HubSpot that automatically updates when a deal changes status? For example, when the deal changes stage, it adds the name of the stage plus the date to a new field. You can then use the New Deal Property Change trigger to change of that property (field) instead of the deal stage. Let me know if you want me to go into any more detail on that or the other option!