The pi runs on a single SD card with a single partition. Swapping SD
card would mean starting over.
If I am to start over, can I migrate the configuration from one instance
to the other?

As a first test you could simply clone the existing SD card.

I am uncertain how to properly run fsck on a mounted filesystem.

You could shut down the system, mount the SD card to another system, and run the check from there.
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