I use a non-retina 27" apple display and a retina 13" macbook pro interchangeably throughout the day. Illustrator seems to handle this fine for the most part. Photoshop needs to be restarted every time I switch — most of the art board will masked out by a black box (this can be fixed by clicking F a few times, but that gets old if you have to keep opening new files). InDesign has a tendency to get buggy menus that won't open when they're minimized or they will disappear completely unless I choose a different Workspace. Anyone else have this problem? The workaround is of course closing all adobe programs when I disconnect from my display, but it is pretty disruptive.
Adobe is still struggling with HiDpi settings. For example GPU acceleration in Lightroom can help with retina displays but UI scaling in Photoshop and notably Photoshop Elements at 200% is limited to Windows only.
Obviously technology is evolving.
Why Lightroom? That's the one program I didn't mention.. just curious.