My initial thought when I read your first post, Ryan, is that there's a huge variety of gear and styles. I could see a quick general guide on the trade-offs of different styles (ie. tent vs. tarp vs. hammock) being very interesting to us beginners, but if you go into any kind of detail, you're going to run into the same problem you mentioned with The Complete Walker, that it's a huge, complex, and daunting document for a beginner (disclaimer: I haven't read any edition of The Complete Walker).

I think other commenters have covered my other thoughts in a much more complete and authoritative way than I could, except for one. That is the issue of this document, be it a book or whatever, becomming out-dated. This will happen for two reasons, first that things change so fast, and second because you're only one person and won't have time to update it, and/or it will no longer be a priority to you. That's why, if you're willing to give up the commercial nature of the venture and do it simply for the love of it, I would suggest starting a wiki. You can have one central series of articles that covers the most important information in a quick introductory way that beginners will appreciate and also have links to satellite articles that provide more detail on certain information. In addition, having a wiki instead of a blog leverages other writers as a resource to keep everything up to date. You can give editing/authoring privileges only to people you trust with this responsibility. Furthermore, even if the entire site is open to the general public, there's always the possibility of selling advertising space.

For my second disclaimer, I should mention that I haven't yet done an overnight backpacking trip. However, I've been researching and slowly collecting/making/testing gear for a long time. I think if you go back to the first post I've ever put on this forum, it was over a year ago. I even mention in that introduction, that I tend to plan and obsess about things for a long time and rarely get around to them (hence my user name). I recognize that doing things teaches you much faster and better than any amount of reading and planning; I fully agree with that thought. Having said that, I think I'm in a position to offer a perspective close to your intended readership, and I will do my best to answer your questions.

Why did you decide to start backpacking?
I camped and day hiked with my family often as a kid, and I remember how special these times together were. I wanted to move on to the next level for as long as I can remember, but I'm not that interested in doing it solo. It was always the combination the outdoors and spending time with friends and family that made it so special to me. For various reasons, it never seemed the right time to start until now. I really look forward to sharing this experience with my young sons, and I hope it will be as much of a special time for them as it was for me.

What do you find most enjoyable about backpacking?
I think my first answer probably covers that.

What makes you the most nervous?
Keeping my kids safe, in spite of my lack of experience. Trying not to obsess or spend money to the point where I cause family tensions. Making myself go through with it, in spite of my busy life, tight budget, lack of support and a hundred other excuses.

What do (or did) you struggle with the most in terms making the decision to finally take up backpacking?
See above.

What questions do you continually find yourself asking about backpacking?
Is my equipment sufficient? What else do I need? Am I overthinking it? Can I really afford it? Is my skillset sufficient? Am I kidding myself that I should even go at this stage in my life?

What do you wish you had access to, but don’t?
I live in an area of the country that is beautiful, and I love living here. But, the summers tend to be very hot and humid, and the elevations are low. This limits nearby hiking opportunities and time frames, especially if you want views of anything besides trees. In addition, while hunting and fishing are big in this area, other outdoor activities are next to non-existent. This means, by the time the weather has cooled down enough that I want to spend more time outdoors (the mosquitoes being a big part of that equation), the fall semester is well underway, which is a busy time for me. By the time things have slowed down enough to take some time off, I've got a pretty narrow time window between that and the beginning of hunting season. So, I wish there were mountainous trails less than four hours away and higher, both for the cooling effect that going higher brings and for the views. The lack of interest in my area also limits availability of good used gear. I would love to be able to go into a secondhand shop and find a lightweight pack or bag that fits my needs, but that's probably not going to happen.

What do you find the most difficult about backpacking? (choosing gear/finding a trail/skills and techniques? things like that)
I don't have experience enough to tell you yet. Maybe I'll get back to this at some point.

I'd also like to second what others have said about what your pack is filled with and how it's packed making a huge difference in how it carries. Even without using a dedicated hiking pack, I know this to be true from using a book bag for day hiking. I usually hike with my two boys, ages six and nine, both of whom have autism. My nine year old is very high functioning; most people who talk to him don't know he's been diagnosed with autism, but my six year old's autism is severe enough that he's still in diapers, so I have to carry a lot of food, water, diapering supplies, and other gear when we go for a day hike. Packing the book bag correctly makes the difference between an enjoyable day and being in pain in short order.