> You are talking about someone who gets zero matches at all
No, I'm not.
> People are far more willing to pay to upgrade a good experience than they are to pay to try to improve a bad one
This is an assumption and one I believe is false. My belief is that people are more risk-averse rather than they are risk-taking [1]. People don't care to upgrade when they're winning.
> Further, an unappealing profile that gets zero likes will continue to get zero likes after they upgrade to a paid subscription.
Not matching with someone does not mean they have 0 likes. The platform just isn't incentivized to show you who likes you for free. Concretely we can take Tinder as an example. They will show you that someone likes you even when they won't show you who. Swiping enough to find the person who likes you usually takes countless hours.
> This user is far more likely to get frustrated and uninstall after a few minutes than if they were to download the app and be shown profiles that are appealing
If you're extending this to anything past the first profiles shown, this is simply untrue. You just need to dangle a carrot in the form of "someone likes you," even when the person liking you is a bot account.
[1] https://en.wikipedia.org/wiki/Prospect_theory