Reddit reviews Windows Internals, Part 2 (Developer Reference)
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Read Windows Internals - http://www.amazon.com/Windows-Internals-Edition-Developer-Reference/dp/0735665877/ref=pd_sim_b_1?ie=UTF8&refRID=0RC78Q7CBY0MX3SQHDNP
It is co-authored by Mark Russinovich who is a Microsoft Fellow. There are two parts to that book, both ~$30, but they provide in depth information on the workings of Windows in a variety of areas.
You're probably going to absolutely hate my advice, but I recommend you read these two books:
Windows Internals, Part 1 and Windows Internals, Part 2
They're very long books, and they can be very dry if you're not interested in them. But if you want one surefire way to learn driver development, it's to learn how the inner mechanisms work. When I first started trying to teach myself Linux driver development (which I feel is actually even easier than Windows), I noticed most of the tutorials I did pretty much went in one ear and out the other. I could write the drivers up and get them working with the tutorial, but I just didn't know what to do next. You'll probably retain maybe less than 25% of the material when you read both those books (probably around 1,300 pages). However, what you will retain is the breadth of knowledge.
When you start working with WDF, you probably won't know nearly anything required to develop your first real driver. What you will know after reading those books though is how to learn. Once you have the breadth to figure out what you don't know/remember, you can easily look it up and figure it out for yourself. If you don't know what you don't know, it's unlikely anyone (including online resources) will be able to help you.
This is out of my league in terms of knowledge, as I don't know the way Unix security is implemented too well but I will say this, syncing Windows permissions to Unix will be easy, just group the write permissions into Windows into a write permission on Unix, the other way though is going to be considerably hard unless you start working with the Unix version of extended attributes, which I certainly don't know about.
For information on the Windows Security system, and how ACLs work, then the Windows Internals 6th Edition books will be your best bet, Mark Russinovich, David Solomon and Alex Ionescu practically know the OS inside and out and they are a great read for learning more about the insides of Windows. Security is in part 1 chapter 6 on page 509 or 487 depending on your reader, but it helps to read through both just in case there are some additional details listed elsewhere.
I've linked the books below on the US version of Amazon, if you are in a different country it should be available using the search box on their, additionally you can probably
Part 1: http://www.amazon.com/Windows-Internals-Edition-Developer-Reference/dp/0735648735/ref=sr_1_1?ie=UTF8&qid=1405718207&sr=8-1&keywords=windows+internals+7th+edition
Part 2: http://www.amazon.com/Windows-Internals-Edition-Developer-Reference/dp/0735665877/ref=sr_1_2?ie=UTF8&qid=1405718207&sr=8-2&keywords=windows+internals+7th+edition
Additionally I think Russinovich has a public email that you can contact him on to discuss stuff if you like. Apologies that I couldn't help a bit more but like I said, the requirements are far beyond my scope of knowledge.