Some tough choices here. My feeling is that at least initially avoiding getting deep into the non-ocP pieces is good. There are other tutorials/whole books on the non-ocP tools. People just need to know what they need. My following comments are a bit more generic:
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I see two browser choices that have enough market share and work "everywhere": Firefox and Chrome. Trying to make converts between them is not going to work.
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on the other hand, having an example of how a page looks in Safari, IE, Opera, ... and even a mobile device is worth having when you are suggesting the site be tested with all common browsers.
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I don't know what is hot right now but I would guess an FTP add-on for a browser would be easiest to explain. That said, I played with graphical FTP clients and decided they were not worth the trouble. As long as I have shell access, scp is my tool of choice.
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I am not a graphics kind of guy but there certainly are cases where something needs to be done. I have always been intimidated by the Gimp but it is the best out there. I was once told that if someone is familiar with Photoshop, the magic key is "when confused, right click". I told that once to a friend who used Photoshop professionally and she was totally happy after that. Thus, I would suggest something like "using your graphics program, ..." rather than trying to solve graphics how-tos in this book.
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I have no clue how to install ocP on Windoze (or how to do anything on Windoze as I have not used it since version 3.1) but I assume it "just works" like it does on Linux. As for hosting, pointing to places with auto-installers would make the most sense. If someone knows enough to install anything on a system without an auto-installer, ocP will not be an issue for them.