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Jamie, did you put a gauge near the booster? And tried breaking when cold? You don't have to be moving just see if it maintains the same vacuum as a warm setup.

Thanks and here is an other consideration we can use science! Put a vacuum gauge on your line to the brake boost, let it sit, start the engine, and then engage the brake. That should indicate a...

Here is an interesting possibility I wonder if you have water in the vacuum system and it is condensation after sitting. Just random thoughts.

So lets say you fixed the mechanical side of things perfectly. Could there be a ABS failure that causing the brakes to loose power? For example the wheel sensor could be sending the wrong speed or...

I used a 2 gallon pancake, it was more than ample to do the job.

speaking of hand pumps. Here is a consideration
http://www.aveoforum.com/forum/f94/using-autobleeder-review-16303/