I'm speaking as someone who has handled a fair share of timelines (with reasonable success) you have pointed out.
To begin with, it is interesting to see you lumping up different kinds of timelines. For example, the cost of not meeting SEC timeline different one compared to demo to be shown in a press conference.
> should we spend $50k announcing at conference Y in month Z, or should we wait until month A?
What is it that you want to announce? Product launch perhaps? Then let's work with the product folks to design it and then take it to engineers to figure out work estimate. Give them time to estimate; if the timelines don't match then reduce the scope.
> Our competition just launched; will we be able to launch this quarter
Sure, they launched this quarter. Do you know how long have they been working on it? If not then it's a similar exercise as above.
> we have to report material financial impact items quarterly or face SEC fines
Why are you telling me this? SEC doesn't ask for such reports overnight. You messed up by not telling us so fine it is. OR there is some human at the SEC with whom you negotiate.
> So show me a methodology that mere mortals can implement successfully.
If there were such a methodology we wouldn't be having this discussion to begin with. It would have been commoditised, similar to a car manufacturing assembly line.
What business people don't understand (or internalise) is software is a truly a new beast. It is a tool that can be applied in just about every domain. No such tool has existed ever in human history. If you want to disrupt a domain then you either develop expertise in it or hire them from the industry.
> If all you can do is complain and point out unicorn 500x engineers (yeah try hiring for that characteristic, good luck), then I don’t want to hear it.
In some cases that is indeed the reality. If you don't even want to acknowledge the reality then good luck hiring good people. If you say point out how Apple launches products like clockwork then I'll point out how they have had close to 50 years worth of experience and all the associated optimisations they have done with their supply chain and what not.
Reality is, whether you acknowledge or not, is full of detail[1]. It can't be bent to your convenience, unfortunately.
[1] http://johnsalvatier.org/blog/2017/reality-has-a-surprising-...