Also, the entitlement from men would be off the charts. Can you imagine how pissed someone would be if they paid $100 to have their message ignored?

They can always pay to express their displeasure—even better if a cut of the price is shared with the user (but that would introduce other issues).

Yes, I think this is by far the biggest problem here. I’m sure there are some women who would enjoy knowing that only those willing to pay the most, would be able to court them. But I would wager that most women would feel differently. Presumably a dating service finds potential mates who are good personality match, not just who are more willing or able to pay.

I don't think so.

The person would not know how much the sender "paid" for the "postage" for that message. From ANYONE's point of view, they are not receiving more than N messages per day, as N+1 would become exponentially, prohibitively more expensive.

This is not an info that you can hide from users for very long.

You will have people who start with a profile in both sides to see how it works. It’s done for fun on free platforms, it will done for research on any paying platform.

If they don’t do it personally they’ll ask friends that will spill the beans.

People will rant online on how much they paid for a single text sent.

It’s just endless, the service will need to be transparent and forthcoming about the system or it becomes a PR nightmare.