I think one of the good things about YC, is if you try to optimize for getting into YC, you're actually building your startup in a constructive manner.
Imagine if FB had a premium plan in 2008, they wouldn’t have made it.
In this case it probably makes sense to charge early on, but it doesn’t look like they did much research on the decision
How would you even research such a decision if not ask very experience startup founders and investors?
It’s not a guarantee of success, but it definitely helps you build the relationships you need to participate in the “global domination” game (which is the game you’re playing, because that’s the game investors are playing).
who's at the top of the HN leaderboard?
It was worth money.
Therefore, they have left a lot of money on the table.
In my opinion, they're still not charging enough but they'll work that out. Keep at it OP.