Illustrator

Raised as a usability problem by 4 people on Hacker News over 10 years (2010–2019), in 4 threads.

People raised many different problems with Illustrator, but no single problem has yet been raised by 3 people in 3 different months and threads.

Unreviewed issues were grouped by machine: Claude Haiku labelled each comment as a usability complaint, named what it's about and summed up the problem in a line, and a small model grouped similar problems. Nobody has checked them by hand. Expect mistakes.

The newest 4 complaints

Illustrator's user interface is clunky to the commenter2019-10-07
Updating the graphical resume is a pain, so it has to be edited manually each time2019-09-17
Each line of text becomes a separate SVG element, so editing text is very difficult2015-03-08
Program is so confusing the commenter struggles to use it2010-02-04