On most interactive web sites these days, it's possible to simply paste a screenshot, rather than going through an upload form. This makes the creation of help pages (and support discussions) much easier. Smoothing the process of uploading screenshots of Wikimedia sites is an area that could greatly improve the experience of creating help pages. This could be accomplished in any of a number of ways. One easy solution would be simply to improve the default choices one sees when manually uploading to Wikimedia Commons to include something tailored to Wikimedia screenshots or screencasts. -Pete Forsyth (talk) 18:39, 21 February 2019 (UTC)
Topic on Help talk:Growth/How to create help contents
Here's a help page that describes how to create screenshots for Help pages: https://en.wikipedia.org/wiki/Wikipedia:Screenshots_of_Wikipedia
What would be really nice would be an interactive wizard for uploading Help namespace screenshots.