I absolutely agree that knowing specific wants and needs makes tailoring advice and guidance much easier. That being said, there are some general accessibility related factors and "commonly used/wanted, or likely to become so" features that make certain programs likely to be better choices than others, and from the outset, if long term use and the ability to get more sophisticated as the needs arise are considered. Almost all of us have personally been through only needing the basics starting out but finding that doesn't remain the case for long. I tend to consider what my own experience as a person and a teacher indicate are common future needs when recommending things like email clients.
To my knowledge I am the only fully sighted regular on this list.
As Chris has indicated, it also helps to have a self-assessment from anyone requesting help about their own level of proficiency with what they have used, and information about exactly when that was and what was used. For example, someone who was really proficient with JAWS 8 and Windows 7, last used 15 years ago, is going to be a lot more like a complete beginner than someone who used (or uses) JAWS 16 under Windows 8.1 or 10.
Brian - Windows 10 Pro, 64-Bit, Version 1809, Build 17763
Puritanism: The haunting fear that someone, somewhere, may be happy.
~ H.L. Mencken