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We almost had this with the Microsoft Courier. Digital notes first, but could quickly copy/paste/undo/take a picture/record sound. It was all about seamless data entry whether in written, audio or visual form. A shame it got cancelled.

I'm watching the Surface Neo very closely to see if they bring the same focus of seamless data entry (and offline export hopefully) to it...if so then not only will I buy it, I will issue it the only passport to my home ever to be issued to a Windows 10-based device.

The Neo smartpen [1] looks great. They claim it can automatically saves a digital version of what you write down. The downside it that it only works with their notebooks.

[1] https://www.neosmartpen.com/en/

What are your main hurdles?