Also, the $20/month subscriptions are HEAVILY subsidized, so it's not an apples-to-apples comparison really

It is a completely reasonable comparison for me as a consumer, since they're the costs and benefits that I'll actually get.

For now yes. But don't count on it staying that way. Even month to month the actual allowances change.

For the amount of tokens you get, based on your comment, ALL subscriptions are heavily subsidized, and the most expensive ones are the most subsidized.

For OpenAI and Anthropic, the $100 subscriptions cost 5x the $20 subscriptions and give you 5x the tokens. And the $200 subscriptions are 10x the cost for 20x the tokens. (Tokens cost 50% as much.)