[thesausageking]

If you lower the ask, you'll get more people to pay, but will it lead to more revenue in total?

In my experience, I don't think so. It's really hard to get users to pay for a free app. If you've gotten them over the activation energy required, it usually works better to ask for more. Users who contribute less also tend to churn more and cause more support burden. So you don't need just to convert 6x more at $10 / yr vs. $60 / yr but more like 10x. And 10x is really, really hard to do, ime. Again, the main thing you fight is getting users to pay anything at all.