I use Org more or less constantly, and I'll take this opportunity to note an Org-related observation that I've been mulling over for a bit. It's apropos of nothing, but then so was this submission :)
The observation has to do with how new Org users get to know the system. The whole thing can seem pretty daunting, especially when you look at some of the examples of TODO setups (http://doc.norang.ca/org-mode.html) in the wild. Pretty crazy.
My nutshell advice for new users is: in the beginning, you should emphasize learning to use Org's tools effectively, rather than spending time organizing your Org files structurally. The initial impulse is: I'm going to make this file look just like my brain (or my project). Instead, learn to use the agenda commands, so that you can make the Agenda look like your project, not the file.
A couple of reasons for this: If you start out trying to make structure (and I'm also talking about very complicated TODO keyword flowcharts), you're going to get it wrong, and it's going to be a pain in the butt to fix. Learning Agenda commands, on the other hand, will always provide you with more flexibility, not less. It will give you the power to handle new situations easily, and to narrow your focus with ease. (Actually the same principle applies to Emacs usage in general.)
For instance: I do a fair amount of event and conference management, little four/five day things. In the beginning, I started by making Org files where each day was a heading, and then the various events lived under the various headings. This meant that, if events got changed around, I had to go to the file and refile, which isn't terrible, but is a pain.
Instead, I now have no day-based headings at all, just a pile of potential events with timestamps. The Agenda organizes things into days for me. If I need to reschedule something, the Agenda provides more than ample commands for shifting dates by hour/day, or simply entering a new date altogether.
Dump everything in one file, all top-level todos. Use the built-in TODO keywords. Learn to make timestamps, and schedule/deadline cookies. After you're good at that, maybe consider using tags (but maybe don't). Spend the rest of your time learning how the Agenda commands work. Stay in the Agenda, and if you must look at a file, do it with <SPC> on the headline (followed by "o" when you're done), or, if you must, <TAB>. Resist the temptation to futz with your files at all, until some real need begins to emerge from daily usage. If you hold out until the annoyance is killing you, it should be very clear what needs to change, and how, and you're unlikely to do something that you'll regret later.
(I should note that I use Org for two general types of work: one is document authoring, the other is todo/agenda management. The above basically only applies to the latter.)
Learn to impose dynamic, temporary structure on your agenda, rather than imposing static, one-time structure on your files.
Here endeth the (unasked-for) lesson. :)