I suggest that you dive into this topic:
In the course of that thread you will find a discussion about Text Expander replacements. One option is Keyboard Maestro.
A lot can be found in the Keyboard Maestro forums:
Regarding the insertion of dates and times:
Almost everything can be done with Keyboard Maestro. The only question is if it should be done with this powerful automation tool.
I think that it comes down to the question to what extent you use text expansion and if you are using it on a Mac only.
To my mind, nothing comes close to Text Expander if you are a multi-platform user.
If you use TE exclusively on your Mac and if you are a heavy user of text expansion, Typinator might be a non-subscription alternative.
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