I don't really have the answers to your questions but I wanted to suggest looking into your state's Bureau of Vocational Rehabilitation/state assistance. My boyfriend is blind and this agency has gotten him assistive technology as well as training in JAWS where someone comes to the house to teach him how to use it extensively. We are in Ohio but I bet there are similar resources in other states.

Hi there. with enough Googleing/researching questions and issues, plus reaching out to JAWS users, I think you may find the learning process easier then it might seem at first.

Remember that you don't have to try and learn all of the random features that JAWS has. Honestly, I think it has way too much going on in it's settings, at least for my specific needs; even though I have been using it off and on for over a year now I am sure I do not know what half of the settings and random features are for. Voice Over on the mac is much more basic, compared to windows screen readers, but I don't think most users have a mastery of all of it's settings and features either, which is not a bad thing. Most users have no reason to use the Voice Over commander to remap hot keys so they never have to move their hands from the home row and are therefore more efficient. yes, this is something I actually did when I was a mac user.

So just remember, poring over JAWS documentation and audio help files is a good idea, but you don't need to know a lot of the available features to become a decent JAWS user. Honestly, I think the OS of windows itself offers a steeper learning curb then jaws, when it comes to switching from the mac. Even though I love windows now, there are a lot of things about it's file system, settings, apps etc. that are odd and inconsistent, and mastering these idiosyncrasies takes time and patience. Once you get the basics of the OS down, Windows Explorer, the desk top, ribbons, the start menu etc. the JAWS part should be much easier, I would think. The experience of using most screen readers in web browsers is pretty similar, with some variations in feature sets of course. Apps can be pretty unique and take some poking around to get comfortable with, just get ready to do a lot more tabbing and shift tabbing instead of using the arrow keys as much. The different cursors you have access to with JAWS can be hard to get your head around, but you won't need to mess around with them too much in most situations; I think this is a very good topic to read documentation about. Read this page if you have not already, it's the first thing that came up when I googled JAWS and cursors just now.

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I really think the main thing you need is just a lot of hands on time and experience. I was a hard core Mac OS user for the first 7 years of my life as a blind person. Despite receiving JAWS training at multiple training centers I never spent much time with it or windows, and I never became comfortable with them. I believe this was because I never used windows in my day to day life, I would only boot into windows during training classes, or when I needed to do one specific task, which is not a great way to become a competent user of anything. However, at one point I was in between jobs, changing careers and I knew I would need to learn Windows for my next job. I finally decided to stick with windows and learn it properly. I decided to only use Windows for a month, booting into Mac OS only when I had no other choice. After a few weeks of using Windows every day I never looked back and I am now exclusively a Windows user.

I do not want this to become a, screen reader vs. screen reader thing, but you might also try NVDA. Personally I find it much simpler to get my head around, and it is my primary screen reader. Either way it's always good to have as many tools as possible in your tool box. Feel free to ask any questions yu have about specific areas; there are lots of very knowledgeable people on this sub reddit.

You can also try NVDA but they don't have a lot of training videos. You can buy some training videos from NVDA but they are real basic.

Hi. I am a JAWS user, and I think that it is important to decide on a few set goals that you will want to decide on when learning how to use this screen reader. I can personally testify that it is verry easy to get overwhelmed by the countless features of JAWS. I would consider what are the main computer tasks that you will need to accomplish with your job. This probably consists of creating documents, making PowerPoints, using spreadsheets, sending emails, and etc. I would first learn the basics of Microsoft Word and your web browser of choice. Using other computer programs will build on your knowledge of these programs. JAWs also has several key commands that are also windows commands as well. I have found it helpful to start by making flashcards to learn how to use many of the different functions of JAWS. Additionally, you might find tutorials by independent organizations to be easier to manage. Many of these can even be found on YouTube. Last but not least, JAWS has a command search function that allows users to quickly look up key commands. You would first press insert and space together. When you hear a chime, just press the J key once. You will then enter a window where you can type in key words such as ‘spell check’, and you will then arrow down to read the directions that explain what keys to press to bring up the list of misspelled words. I hope that this helps.