Glad to see I'm not the only one that wanted this workflow!

I added this the first cut of this feature to iTerm2 about a decade ago because I often work in the terminal, but sometimes need to reference files elsewhere in my workflow. The feature was named "Semantic History" although in hindsight, it's not a very good name.

To use, hold Cmd and click+drag the path to where you want to drop it. Behind the scenes, the current working directory is stored with the position of the buffer, so it works on relative paths even when you change your working directory. On Cmd+Drag, it searches the buffer around the cursor until it finds a valid path to work with.