I actually found the transition pretty easy, but then again I'm a young person (29) who has been using computers since age 10.

What I appreciate most is that while Jaws and other screen readers for Windows are 3rd party application software, Voiceover is baked presumably into the kernel of the operating system. What this means for the user is better integration. All of the native apps on the mac are accessible, and crashes/freezes caused by the screen reader are far less frequent.

I find navigating GUIs much more intuitive as well. With Jaws, we typically have to iterate through all of the elements of a desktop app according to their tab order until we find the one we want, unless it's available either as part of a menu or includes a keyboard shortcut. With voiceover, things are presented according to a hierarchical tree structure, allowing us to quickly skip over entire logical groups of elements. To illustrate, let's imagine a fictional music player app with the following features:

1. A group of controls featuring play, stop, pause, rewind and fast forward;
2. Another group including previous, next, repeat and shuffle;
3. Another group including song title, artist, genre, playtime and remaining time of current track;
4. A playlist widget which contains a list of queued tracks, add and remove buttons and buttons to move the selected track up and down the list.

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That's nineteen different UI items across four different collections.

If this were on windows (and assuming there weren't keyboard shortcuts or menu items to interact with each and everyone of these controls), to access say the track name field I might very well have to tab (or shift tab) through up to ten of these items to find the one I want.

If this were on the mac, given that these items are grouped together, I could simply press control option right arrow (VO+Right) to skip over entire groups until I reach the group I want, followed by VO+Down to enter that group, followed by VO+Right to navigate through the controls in the group until I reach the one I need to activate with VO+Space.

When you know a website or app well this becomes noticeably more efficient. I especially love when webpage ads are nicely locked away in a little frame and Voiceover lets me just jump cleanly over them.

You will also find that Voiceover is available almost 100 percent of the time. Even during system updates you can turn it on and find out what's going on. Even if an unlikely scenario occurs wherein you must reinstall the entire OS, Voiceover is available to guide you through the entire process.

In summary, I bought the mac because I was studying software development in college and needed it to make my skillset more well rounded. I thought I would only use Mac OS for mac programming. Since I started using it however I have felt as though I would never go back if given a choice. Let him spend some time experimenting with your Mac before making the considerable financial commitment.

The nice thing at least is that you can use "bootcamp" to run Windows on it if he decides he doesn't like it. It's still a very good laptop no matter what it's running.

I wish it was easier to try OSX for cheap.

Voiceover is very easy to learn I found, coming from windows about five years ago. The next version of macOS is supposed to simplify some aspects the way voiceover interacts with the system in 10.15.

Its really not too bad. Voiceover has a lot of help documents to read and a tutorial as well, and also drops hints after a few seconds on an item for what to press etc.

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