Switching from Jaws to VoiceOver

In my experience, the answer to your question is no, but it really depends on how you use your computer and what you use it for. If you only use it for checking emails, browsing the web, and watching movies, then you'll be fine. If you're using a lot of third-party applications or writing long documents, then I would think twice about it. There is another thread that discusses that in greater detail which I will link below.

As far as switching from JAWS to VoiceOver goes, I didn't find it hard. It depends on how open you are to learning a new system and realizing that the UX is completely different. If you can forget what you know and come at it with an open mind, you can easily learn it. That doesn't mean that you will like it. Only you can decide that, but you can learn it. The UX is also different from the iPhone.

I learned it. For a year, I only used a MacBook for work. I was less productive, had more accessibility issues, and I was often more frustrated. The pluses of being on the same eco system with all my devices weren't worth the hassle of the MacBook. In my opinion, accessibility on the Mac is like an old house in disrepair. Pieces keep falling off of it. The roof leaks, and it keeps getting worse. The windows and doors need new weather stripping, and I could go on and on. Unfortunately the landlord is still getting paid by the renters and doesn't care to make the repairs that need to be made. Accessibility was once smoother on the Mac but over the last several years of OS updates many things have broken that haven't been fixed.

This thread was from a month or so ago and may answer some of your questions. Also, I just read my post on there, I can tell I was half asleep and writing it on my phone. https://www.applevis.com/forum/macos-mac-apps/getting-mac-few-questions

My only addition to Cowboy's reply would be to say that using VoiceOver on the iPhone won't probably give you too much of a head start with VoiceOver on Mac unless you have been using an external keyboard with it. They are two quite different beasts in my opinion.

One advantage, however, will be from a familiarity of how some applications and features work. You would also potentially benefit from a similar familiarity with Apple's concept of how things should function and how they think you should use them.

From my experience, if you are willing to spend a little time discovering and learning new approaches and tools, the transition should be relatively easy unless you have a very specific and demanding use case.

Good luck if you do decide to take the plunge ☺️

Do check out that thread that Cowboy suggested first, though.

I jumped ship at the end of 2013 and acquired the MacBook Air on which I'm composing this reply. I have to respectfully disagree that VoiceOver on the Mac has gone downhill. I am not a Braille display user, so can't comment on that. But my experience and use case have been the total opposite. I don't think I'd consider myself much of a power user yet, although perhaps I'm getting there. I started out on OS X Mavericks, and now I'm running Big Sur. We'll just have to wait and see about Monterrey, but in my opinion Apple has done a great job. They seem to fix VoiceOver bugs pretty quickly. They are a huge company and accessibility is not their only fish to fry. Fast-forward to 2018, when I got an iPhone Seven. I've been very impressed with VoiceOver on there too, and this little hand-held device is extremely powerful. I believe I'm due for another Mac one of these days, but not sure exactly when. Hth and best of luck to you with whatever device you choose. Thanks for sticking with me in this long-winded response.

I also really enjoy the MacBook I wonder if you're the guy from YouTube that was asking me about this recently? Anyway there is a shortcut that you can do if you're on a webpage you can do VoiceOver plus Q it will say single key quick NAV on once that happens you can then just press h for heading etc.
In my opinion the Mac accessibility has been really good especially for free. There's programs on here I can't use on windows such as Audio Hijack they give you so much more versatility than any windows recording program ever. Unfortunately I do agree with the word processing the only thing I found that's relatively close is Ulysses and that's pretty good! However if you're using the computer for work that probably won't fly.
Finally one other command that you may like is under VoiceOver general utilities by pressing voiceover plus F8 you will find a modifier that allows you to use the caps lock instead of control option which cuts down on your key presses.

I chose a MacBook Air because I wanted an absolutely silent cool laptop and there is no such Windows machine. I also love being able to copy from my iPhone to my Mac, Keychain password management, and other integration.

I miss JAWS, especially the scheme reading tool and speech and sounds manager. VoiceOver doesn't even seem to be able to tell me the font color and characteristics on web pages. That only works in editors. Since NVDA never had these things I have no use for it. I prefer VoiceOver to NVDA but JAWS is mostly better than Voiceover. JAWS and Windows are pretty sluggish beasts, though. I prefer Mac OS to Windows.

One of the biggest problems I had with browsing has now been fixed. Browsing with VoiceOver was positively defective for a while because VO focus would constantly get stuck or lose your place. It's fixed now. Both systems have their issues so it's hard to say what is best.

If you switch it will definitely take time to learn and you will want to become very familiar with modifying Voiceover commands and settings to suit your needs. I also recommend LaunchBar by Objective development as a productivity tool for Macs. It allows you to type a few letters to accomplish different tasks or find things. It is also a clipboard manager.

I answered this question several times, and I think the best answer is: if you can, try a mac by yourself for some hours before purchasing, or just ask for a refund if you are not happy with the device.
A lot of users are very familiar with an iPhone, decide to switch, and some days later they realize things like:
- Productivity decreases because you need more keypresses for everything.
- Office work, specially text editing is harder.
- Less apps are available for your needs.
- Almost no games.
- Problems with webapps like mail based clients, google docs, etc.
Just to mention some common problems.
They all can be solved, more or less, but even after years of developing software on a Mac, I feel like am playing with a hand tied to my back. IN fact, a couple of friends of mine finally decided to buy a Mac, and when they realized how faster was their workflow with a Windows machine, it was too late and the moneyback guarranty was not there anymore.
In my very personal opinion, a Mac doesn't worth your money unless you really need to develop for the Apple ecosystem, but in any case, it's not for everyone.

I found this tutorial very useful, has some great tips.
https://www.youtube.com/watch?v=6y6MQq-Jtz0