I wouldn't worry about JAWS to be honest. Wrap your head around NVDA's browse vs focus mode to really *get* navigating the web, and work out how much you need it to tell you about in the document presentation section of NVDA's preferences. I turn almost everything off - I don't care to hear when something is a heading, for example, not most of the time.
They have superb training materials, their basics one gives you many useful shortcuts. I'd be very happy to answer questions if you go through them, or come online with you and do stuff together at some point if that would be of any use.

Just to come back to some of your other points ...

* touch screen Internet access was new to me; until comparitively recently: I transitioned from a button phone. I miss t9/"predictive text" input. that said, I've been using a Virtual-cursor approach with screen reading on the web for almost 2 decades now, so that feels very familiar.

* the Orbit is probably one of the best options for Braille if you have to fund it yourself. It can be an invaluable tool for proofing and an excellent aid to do more Braille learning, and they also make for great notetakers in their own right due to their remarkable boot-times. You'll have complexity moving content written on an Orbit into Windows/Android though, as it saves in a braille format generally speaking, or even if it does translate, only into plain text.