Richard
(Richard Fairhurst)
4
Well, I wrote the osm2ai.pl stuff, I use a Mac with Illustrator, and I work as a magazine editor. 
It’s not particularly easy to use, I’ll grant you that. It works for me and so I just put it up there so that others might be able to benefit. I’d like to add it in a user-friendly format to the Export tab, but right now I haven’t really got the time to work on that, unless someone can set up a read-only database on dev.openstreetmap.org that you can query directly.
I know Frederik at Geofabrik has played around with the osm2ai.pl script because we’ve had some conversations about it - worth contacting him, I’d think.
Failing that, let me know what area you’re looking at and I’ll see if I can help.