Not being able to run a 15 year old codebase on a < 1 month old runtime without making some modifications has nothing to do with static or dynamically typed languages.
But first - why don't we point out that the bulk of the issues the author faced had nothing at all to do with types? The issues were primarily with syntax changes.
Regardless - with a statically typed, compiled language, you find these issues at compile time. With any other language you find them at runtime. Either way, you'd have to fix a whole lot before you deploy the code, and just because you prefer to find your exceptions at compile time doesn't mean that it's the best way to find them.
I think it's really strange that the headphone jack wasn't mentioned at all in the review. In the one instance he refers to it he says "where the whatchamacalit jack used to be".
Your steps sound nice but in reality it doesn't work out this way (speaking from multiple experiences with your reputation system).
First of all, EVERY piece of desktop software my company delivers to users is signed via a known and trusted authority. We knew that would be important and took steps before ever releasing our first piece of desktop software.
Secondly, the error message that users are presented with SCARES THEM. It's not clear why the software is being blocked, and in most cases the user just abandons the software instead of calling us to let us know there was an issue.
When we finally did discover the issue, it wasn't clear what to do. It took us quite a while to figure out where that "false positive" link was, and we weren't even sure that it was the right place to send it to. Even worse, you claim that they "should" have the programs whitelisted within a few business days. This is patently false and never happens that quickly. It took a month before the executable we submitted was whitelisted and you know what? It didn't help one bit.
Symantec seems to not take into account the fact that the executable will be updated, so by the time our first submission was whitelisted we had published 2 updates adding features and fixing bugs. Those updates were blocked even after the initial executable was whitelisted.
You may not be "out to squish the little guy" but honestly that doesn't mean you haven't done quite a bit of damage with your lack of clear messages to your users about why a piece of software is being blocked, and not allowing someone to easily choose to ignore your suggestion that something might not be safe just because symantec hasn't seen it before. (By the time our first symantec using user installed our software we had an installed base of over one hundred users)
But first - why don't we point out that the bulk of the issues the author faced had nothing at all to do with types? The issues were primarily with syntax changes.
Regardless - with a statically typed, compiled language, you find these issues at compile time. With any other language you find them at runtime. Either way, you'd have to fix a whole lot before you deploy the code, and just because you prefer to find your exceptions at compile time doesn't mean that it's the best way to find them.