Do we have to "make" a new .pdx every time we want to test a code change? (Windows)

Short answer: yes.

A game project needs to be compiled into byte code and assets converted to be used in the simulator or playdate. Based on my experience this is typically pretty close to instantaneous even for bigger projects, so I never felt it was slowing me down.

Usually I am in my code editor and I have a build script that prepare the pdx and launch the simulator automatically.

But that depends of what editor you use to code.
This is an extension for vs code but I don't know if this is still maintained

And I shared my build script for Sublime Text

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