Thank you very much, this is helpful.
I have created a special version of Stripe Payments plugin with extended logging functionality. It should help us determine when exactly the things are going wrong during the payment process. When we get this kind of info, we’ll be able to understand why.
Please install this testing version https://s-plugins.com/testing-version/. Don’t get alerted by the “testing” thing, the version is only a bit different from current stable version (2.0.44).
Now, if payment error occurs, the debug log would have the additional info we need. It should also have the info that customer entered to the custom field, so this should help you to process those orders internally as well.