Bob wants to get into writing, and he has an iPad to do it. Leo says a computer is a much better option than an iPad. That virtual keyboard isn't very comfortable. What software should he use? Leo says that there are plenty of word processors out there, many of them are free. Notepad, on Windows, is a good basic word processor. But Leo really likes Typora. It has a ton of great features including word count, lists, and markdowns. But it's basically designed to encourage a free flow of typing without getting bogged down.
But a computer also offers a lot of distractions from games, the internet, etc. A lot of people are recommending JUST TYPE. Another good one is Scrivener. It's about $50.
How about dictation software? Leo says that all operating systems have voice dictation built-in. It's enabled under accessibility settings.
Should he upgrade to Windows 10? Leo says YES. And he can upgrade from Windows 7. What Leo recommends is downloading the Microsoft Windows Media Creation Tool to a USB key, and then run the installation from that.