Creator here. Although the site hasn't been updated in a while Write isn't dead - there will be a major update coming out in a few months.
If not, I understand. This would be a really great open-source project that could be trained to automatically produce transcribed plain-text that could be copy-pasted into other applications.
Using a closed triangle as an arrowhead does trigger shape conversion, but I don't know anyone who draws arrows that way.
It's called "Ink to Shape" on the Draw tab.
2) if I could do this with PDFs, or have an engineering graph paper background, that would be glorious.
You can also set the pen to snap to the grid on the graph paper that makes drawing quick block diagrams really easy.
I'm curious what sort of things are in the pipeline? Very grateful for the work you've done so far!