We'll never know, because he's not even trying.

Here's a nicely readable transcript of what they wanted:

https://news.ycombinator.com/item?id=12817061

None of them sound particularly difficult to answer. Maybe they are difficult to answer in sufficient detail to satisfy the NHTSA, but you can always start out by answering them as best you can, and then seeing if they want more. There are people on the other end of this letter, not some unthinking machine. Toss off a quick response and say, "If you have any other questions or need further detail on the answers given here, please feel free to contact me at any time."

If he gave them the docs he certainly has on this stuff, and said "i am glad to sit down and walk you through any other answers or questions you may have", they'd be fine with it as an initial response.

I think you have pretty much already assigned a negative agenda to NHTSA, when they've just requested some info.

While they may have followups if they don't like the answers they get, of all the agencies you find, NHTSA is not one that tends to have a serious pre-bias towards anyone.

I more thinking "why the hell doesn't he have the answers already?"

Having mentioned this elsewhere, I have first-hand experience going between SMEs and X/Y/Z bureaucratic entities for half a decade and there's a big difference between "having the answers you think are satisfactory" and "providing answers that they think are satisfactory." GI Joe pointed this out long ago in that "Knowing is half the battle" and putting it into a work product that accomplishes its task is the other half of the battle in this case (with no guarantees the responses provided will end the inquiry / threat of fines).

That doesn't really answer the question. You don't need first-hand experience to know that government red tape is onerous. It was flatly predictable that the NHTSA -- the government agency concerned with roadway safety -- would make such inquiries. So why didn't Comma work with the NHTSA and get their blessing before announcing a release date?

I mean yeah, it sucks that the government is so darn picky about things, but that's not an excuse to just skip the process. They should have hired someone like you from the start to ensure that their ducks were in a row when they were ready to release.

This, it's not a secret that NHSTA is interested in self-driving cars and would be asking the serious questions that he should already have responses for.