Have you considered training a model on your handwriting?

Yep! However that needs a ton of labeled data, so a bootstrapping method is required.

I like the idea of doing it by speech recognition, or of chopping it up for privacy and then outsourcing that to humans at cost.

One thing I … Imagine … would help—is having a private web app where I could pull up a document and then make a voice recording on my phone.

Maybe I’ll put this together on my plane trip.