Nicely put KurtE.
Personally, I use the bookmarking system provided to keep track of interesting posts I run across and are relating to the segment I am working on, and I still find myself digging back through all the forum posts to find what I thought I read where as I progress to next tasks.
If edison was good-to-go out of the box for everyone, there would be no problems - 1 page instructions. But in that no one should try to be everything to all, there are times when issues arrive.
It is not for when there is no issues that you fill a simple document with too many if this and if that -- but all the if this and if that, why was this, why was that, that is definitely needed when issues do arise. Personally, I started with a bad mini breakout with no OTA drive functionality, had to get a second mini breakout to change the modules over to when I need to flash. Then configure_edison does not connect to wifi when wep_keys contain none ascii values (configure_edison --wifi only allows for string valued password, and doesn't accept hex). And but of course, half+ of the posts on the forum are people experiencing problems that they'd otherwise be off elsewhere and Making.
So for my two cents (or nickels now in Canada as our penny is gone), a task might have a quick-guide for the 90% that go through without any issues, but it would be good for that to also include an updating troubleshooting section that links to the deeper why's and how's of what that quick-guide was suppose to accomplish. What happens when there is no OTA drive access? etc.
Another suggestion would be some sort of acknowledgement section where known issues can be confirmed, looked up and the fix located so that we know that this issue is actively being looked into, and a status/estimate of progress for the user's issue.