For Mac OS System 7 and apparently the context is the Mac OS on iPad Pro from the discussion:

https://news.ycombinator.com/item?id=44942954

as much as I love to run Macromedia Freehand MX, I'd be hard put to choose running it in an emulator rather than a native application such as Serif's Affinity Designer

https://affinity.serif.com/en-us/designer/ipad/

which is apparently quite nice w/ an Apple Pencil.

That said, I'd be interested in a similar overview of contemporary vector drawing programs for Mac OS X and the iPad, since Windows 11 has me wanting an alternative to my Samsung Galaxy Book 3 Pro 360 and Wacom EMR stylus and toggling the Windows Setting which allows me to run Freehand....

Just seeing those names brought back a lot of memories. I was especially fond of Superpaint and Deneba Canvas. But I also got a lot done with MacDraw Pro, which I think at the time was considered limited.

Still love OmniGraffle which itself is getting long in the tooth but still has one of the nicest diagram layout engines I’ve used

My favorite Mac drawing program back in the day was MicroFrontier's "Color It!" https://www.macintoshrepository.org/110-color-it-3-x