I have done research on Ask Different to see if this has been posted and to the best of my knowledge nothing this specific. I reviewed this but that question is more general.
So imagine that I have 10 (or more) Evernote windows and I want, with one shortcut, for all of them to be resized to half the monitor to the left. And then I have 6 terminal windows and want them all resized to a quarter screen to the upper right (different shortcut).
PS: What I currently use is SizeUp and it works great BUT in the case of the 10 Evernote windows, I'd have to use the keyboard shortcut 10 times.
Best Answer
After testing Stay, I think it does what you want. Just launch your desired apps and store all open windows. You can then restore them on Stay's menu bar icon, with a shortcut key or have them restored automatically, when you launch each of the apps in question, or change displays.
I emailed Matt, Stay's dev and this is what he had to say about automatic restoration when launching apps and window title pattern matching: