Were I you, and if I had access to a sighted assistant who could likely do the steps necessary, I'd have them start the process with the screen reader active so that you can hear the steps in action. It has been my experience that very often major problems are the result of one minor omission when trying to do something, even if that omission is not well-narrated by the screen reader, that once you know it's there and you need to do it all starts going along swimmingly.
That, or try to do what you were trying to do with your sighted assistant watching and identifying for you where/when "the breakdown in the process" occurs.
Either way, I suspect that once the problem area is identified it will be simple to work around it afterward. Often that's much easier to do by sight and there's no shame in looking for assistance when you need it, and that's whether you're blind or not. It can save hours to days of frustration.
Brian - Windows 10 Home, 64-Bit, Version 1803, Build 17134
A great deal of intelligence can be invested in ignorance when the need for illusion is deep.
~ Saul Bellow, To Jerusalem and Back