It’s a great question, Chris! I think I agree with you that it can be more challenging for masters in a field to remember what it was like at the start.
There’s one trainer I’m learning from who I think is a master in his field and I’m getting so much out of it because he’s tying it all together! However, it’s very fast-paced and I definitely need to spend time reviewing things on my own or together with others because we get so much content every time.
In contrast, it might be easier for me to learn the basics from a trainer who’s competent (but not a master). However, that person would probably have a harder time explaining how it all fits together.
In general, if we look at successful coaches (say, in sports), not all of them were masters in their area before. For instance, the coach of Germany’s men soccer team wasn’t that distinguished a player himself (if I remember correctly) but he got his team to win the World Cup 2014 (let’s just pretend 2018 never happened…).