Few years using Blender and still not able to do that simple thing

I haven’t read the whole thread, I hope I’m not repeating here needlessly. Thought I’d throw in some of my insight as well.

  1. Not that specific case maybe, but for many cases like that I find the OffsetEdges addon (works with 2.80) as my goto solution. It’s pretty reliable

  2. SHIFT + V to slide vertices, while in slide press (and keep) ALT - now you can extend the slide beyond the edge limit.

  3. I see you found TinyCAD