Assuming this is a heterosexual cis man.

If you are rich and you hire a human to do this for you, is it SA? I have heard of wealthy people who have their assistants do this. Especially on gay apps where quantity is the game.

I don't think that is inherently SA, but it could be, depending on what was said in the chats. If the assistant didn't know something about their boss so just made stuff up. (Its a bit of a different dynamic with gay hookups because much of the negotiation is explicitly conducted via the app rather than in person. It can be very terse but functional.) But if the assistant is just saying what their boss would have said and knows him well enough then idk. I wouldn't personally want to be involved with someone like that but tastes differ.

In a gay hookup its plausible to conduct a short negotiation online, meet up at an agreed location, say nothing or almost nothing, have sex. I doubt this is happening much with heterosexuals, so this guy will still have to do the in person work of communicating IRL with the woman prior to sex. He still has to go on a date.

Assuming this chatbot can be programmed to only say things that are accurate and not fill in the details with wild hallucinations, I have a hard time seeing an argument. Reading the chatlogs would be informative and might change my mind.

however

To get 10 dates, he must have spammed 1000s of women. I don't believe this chatbot has any special technique making it especially good at flirting. Assuming the guy must have good pics, tall, making high income. But still it is a numbers game. If not already done, tinder and similar ought to ban such use of their systems because it will render them less usable. It should be easy to detect this kind of bulk traffic in a single account.

He says he "got" 10 dates but did he "go" on 10 dates? Those verbs are far apart from each other. How likely are they to be actual humans on the other end of it?

In other words, it can't be SA if there is no physical interaction.