IMO 500+$ bikes are far more about fun/ego than transportation. A cheap bike that let's you comfortably travel 3 miles and not really care if there stolen is worth a lot. A bike that weighs 10lb's less but is more likely to be stolen and costs 2-3 times as much is far less useful.
Even for short distances, a better device is more pleasant to use. Not sweating is worth a lot if you can't shower at your destination.
And what if you want to travel 10 miles? Or 50? Carry more cargo, climb steeper hills? I think you should adopt this moderate position from a competing industry: "your mileage may vary."
A cardboard bike is probably not great. Bt getting people on bikes is important. If they have an okay experience on a lousy $10 cardboard bike then there's a chance that they go on a buy a bike and use it.
And, like everything else, there's a lot of nonsense spoken about bikes.
Most people do not need carbon fibre frames and titanium widgets etc.
That's assuming it's still there when you want to use it. A well maintained cheap bike might take 5% more effort to use, but being able to use it in more places IMO is worth more than being slightly less tired when you get there.
I bought my commuter bike for about $550 new. I've had it for 6 years and commuted daily on it along with other 30-40 mile rides on it as transportation (not recreation). The only parts I've had to replace are the tires, brakes and chain which are normal wear parts. I ride in the winter as well, and had I gotten a cheap bike instead I would have spent more money replacing bikes, and it would be a slower and less enjoyable ride.
I do live in an area where a single U-lock is enough theft deterrent, which removes the theft concern for me. Without the theft concern I now have a bike that lets me go farther, carry more and lasts longer than cheap bike. That seems like it's a whole lot more useful to me.
I agree that it's a somewhat arbitrary line and limiting yourself to 100$ bikes is probably overkill for most people on HN. However, I would be shocked if the extra 60$ over a great 490$ bike really made that much of a difference in terms of utility. Still, averaged over 6 years it's not really worth worrying about, but you don't get to guess how long you will use the bike ahead of time.