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Thanks for the detailed reply. Sorry I didn't reply any quicker; I was on holiday abroad.

You're right of course about the magical moving around of tasks; probably not so intuitive.

I wasn't aware of the start -> start dependencies. Those are probably much better for my purposes and will solve many of my problems.

I have already broken down the tasks into lots of micro tasks, but that doesn't really solve the time estimation problem.

My basic problem is that it's very hard to accurately judge how long a task will actually take to accomplish.

I'm sure as a developer you have run into the same problem: you need a nice calendar control but you don't know whether the built-in Mac OS X control is up to the job or not. If it is the effort is half a day, if it isn't you're heading for custom developing the control (40 man days?).

Breaking the task down into "evaluate standard control" and "develop custom control" is better planning but does not provide you with a more accurate estimate of when you'll be shipping your product.

I guess what I really want is something that lets me capture my tasks, define basic dependencies and then work out what I should/ could start working on today AND when I'll be shipping the product based on the current task progress and estimates (e.g. is a september release still realistic?).

OmniPlan isn't really the right product to do that with. OmniFocus is great, but as far as I can see it doesn't really fit the bill either..

I'll see how far I get with the start/start dependencies.

Thanks for your time and thanks for listening.