The biggest issue, speaking as someone who has used computers quite a lot both with and without sight is that it's so, so slow. It's painful. It's a massive frustration to people who have recently lost sight, which is one issue, but certain things, like finding your way around an unfamiliar website that hasn't had a lot of work put into accessibility, is just a huge practical obstacle. If people only knew the level of time that gets wasted they'd write better websites.

The web is a big stumbling block, because of the way a screen reader virtualises a page.
Also learning basic keyboard navigation is surprisingly difficult, the keyboard concepts behind onscreen windows and controls is often neglected

It’s mainly learning how to interact with the computer using a screen reader. Each screen reader has its own keyboard shortcuts to interact with the computer. Thus,, it makes it difficult for users to use different screen readers. For example, if somebody uses Jaws for Windows and try to use a different screen reader to interact with a computer, they try to simulate the same experience with the previous knowledge of sed screen reader. The psychological part of it is that people do not adapt well to change. Such as in this case, a screen reader. However, in your case, you would have to learn how to use each screen reader to interact with a computer and teach how to use sed screen reader.

Screenreaders convey information to the user, but not where that information can be found visually by default.

People who go blind will miss being able to just reach out and target the control they need the way they are used to with a mouse. Screenreaders work more sequentially; you go down the list or tree or page or document until you find what you need, and you have various ways of speeding that search up, but those ways are entirely alien to what a fully sighted person is used to. e.g. you can get a list of only links, or only buttons if you know you're searching for one of those, but that list follows the programmatic order, not the visual one. So something visually at the top of the screen doesn't necessarily have to be at the top of that list.

The best advice I can give, really, is to use the information the screenreader provides it's users. Read the manual, find tutorials and other things. Don't try to relate it to how a non-screenreader user uses a computer. You will have a very hard time bridging the gaps.

I lost my sight as a teen in the 1990s. The two main issues for me when having to relearn the computer as a screen reader user were learning to understand synthesized speech, which was pretty slow going for a while, and, learning the layout of various windows, programs, and dialogue boxes etc without being able to actually see the visual layout. I was a Mac user until college when I was forced to switch to Windows and that was really frustrating for a long time! Now I am fine with both operating systems but it was rough going for a while. It does take time but like with anything else, the more you put into it, the more you'll get out of it!

You have a lot of good comments I reached out to tell you there are many ways to learn about these things many training courses and you may want to look in to certification of assistive tech for the blind or hire someone who is ready to do this job. In many ways this will help you learn what they struggle with and how people deal with it or how you can teach them.

I still have vision so haven’t tried jaws or nvda, but I have recently started learning voiceover, so I can comment on that at least. One of my biggest frustrations has been that for some reason a lot of video tutorials on how to use it seem to reference visual things, like the videos are meant for sighted people or something. Maybe that’s because I’m used to processing information visually though, so that’s what my brain cues in on...my blind tutor tells me it’s all accessible to him. But for someone making a sudden shift it can be really disorienting. Having someone familiar with the functionality show you, or talk you through it live is incredibly helpful. Thank you for providing that service!