I really like the idea of "doing my homework" ahead of time, when I'm in an alert and positive state, and once I have my priorities set and organized, trusting my subconscious and conscious to make good decisions.
10. Don't Take Switching Penalties Into Account. I incur a high switching penalty when moving between complex tasks. My brain really needs at least a few hours on one task to do good work. I didn't see a mention of this in GTD, but using context in OmniFocus can help here - and OmniFocus can generally help me not be distracted by the short term shit I have to get done when I'm working on long-term, creative, and fun things in the mornings.
11. Overly Ambitious. My lists are often too ambitious and not-realistic, resulting in more stress. I think this is more of a personal issue than an OmniFocus + GTD problem!
12. Uncomfortable Things Get Avoided. To-do lists make it easy to avoid uncomfortable (which typically means important) tasks and kick them down the road from week to week. Again, I think this is more of a "me" problem to work on - although, weekly reviews of projects could help with this.
13. Reactive, not Proactive. With to-do lists, it's very easy to adopt a reactive mindset - "these are the things I have to do this week". The GTD Capture, Clarify, Organize, Reflect, and Engage methods definitely help here - sometimes I find myself reacting to and trying to work on "stuff" at the same time, OmniFocus gives me the nice option of throwing it in my inbox and processing it when I'm ready.
14. Unbalanced. Some tasks are creatively restorative, while some are taxing. Writing code and running are very well balance activities for me. I'm working on figuring out ways to use OmniFocus to create more balance in my life.
15. No Sense of Time. No daily, weekly, monthly demarcations. OmniFocus clearly overcomes this limitation of To-Do lists.
16. Created and Executed in Different States - At the beginning of the week I'm too ambitious, by the end I’m just trying to get shit done. For example, last week Monday-Thursday we're well paced, wonderfully productive, and relatively low stress - and then Friday hit and I suddenly had 18 tasks that day. I think just seeing that list set me up for a less focused day - and the prophesy fulfilled itself - I didn’t nearly get done what I had hoped. I think the way GTD suggests dealing with this is weekly reviews - you want to review your projects when you're level-headed, not buried. And when you are buried in the middle of the week, you have the "map" you made yourself to rely on. This is area I could definitely improve in, too often I become overwhelmed and change course in favor of dealing with short-term things.
17. No Room for Multiple Approaches. Often, the first way I try to achieve a result doesn't work. Only though trial and error, and changing my strategy do I get where I want to go. The GTD method of clarifying and determining what the next step is, while not actually doing the step, before hand ("homework"), is really useful here. Multiple approaches are fine, but it's better to sort things out a bit in advance, and not while distracted by the work itself. Processing task and prioritizing time is a project in itself, and should be given the full attention it deserves!
GTD + OmniFocus will not solve all your problems, but are excellent tools based on sound and simple principles. Thanks again to the readers who recommended them!