The magic of EXPERIENCE...

I have no reason to doubt (or trust) that you have the skills required to be the captain of a Superyacht right now. What I am saying is that you'll, no doubt, have to prove them aboard a vessel while acting as a junior officer before being tapped for command. Owners, Management Companies, and Charter Brokers are not likely to roll the dice on someone who hasn't proven themselves in the yachting industry.
You may be fighting an uphill battle due to your age, but you've a much greater hurdle (although surmountable) because of your commercial shipping background. You'll need to show that you have what it takes to run a yacht before you're given one of your own.

Imagine this scenario, and ask yourself how you would handle the situation:
EVVIVA is a 50m yacht with a 10m beam and 2.4m draught. She's FRP construction, and the running gear is exposed (not protected by a keel).
Yesterday, we visited the island of Vulaga, Fiji (pronounced, and sometimes spelled, Fulanga). The only available chart is BA 441, which is scaled at 1:400,000, so it is unusable for passing into the lagoon. The pass through the reef is 50m wide (with a 90-degree dogleg), and has depths ranging from 1m-10m, with breaking waves on either side of the pass. Slack water lasts for roughly 15 minutes, and is unpredictable as the closest tide station is 175nm.
I have first hand accounts, from captains that I trust, that the pass is useable with caution given to multiple coral "bombies" in the pass. I trust these captains, but my boss doesn't know them at all and has no reason to trust third-hand knowledge when it comes to his safety. He wanted to visit this beautiful lagoon, so we decide to enter with caution. Throughout the transit my boss was standing over my shoulder, offering advice the entire way through the pass. All the while, I have one crew member passing advice to me from the bow, and my First Officer glued to the sonar and giving me readings.
Did I need the boss' advice as well? No. But it made him feel more at ease to be standing there giving it.

Some captains would be annoyed or intimidated by the boss watching over like that. (Would this ever happen on a commercial ship?) But it's my job to make him happy, so if that means involving him in the navigation then so be it.

This is one small example of my day-to-day responsibilities. Again, I don't have any reason to doubt you could do well, but that would need to be proven.

I imagine it's a mixed blessing having a boss with so much of his own experience.

I did not say that I considered it dangerous; I felt it was an easily managed risk. If I was uncomfortable with the risk, I would certainly have the last word and we would not have entered. As a matter of fact, we did attempt it the day prior but arrived after the tide was running too strongly. So we went to a nearby island and waited for the next morning.
I mention the story to point out that, while I was comfortable making the passage, I had an added distraction of my boss looking/breathing over my shoulder while navigating the pass.

You hit the nail on the head.

Your thread title says it all "The Magic of Experience".

I am not qualified to discuss operating large vessels. I am merely a weekend motor and sailing skipper up to 50 feet.

I have, however, spend decades as a ski pro for clients. I taught ski technique very seldom, I created passion for the alpine experience non stop. I did that because I am have passion for the alpine experience myself. I happen to be a great technique coach too but my friends that are alpine coaches will not likely translate to client ski pros. I see some similarity in the Luxury Yachting vs. Merchant Captaining.

In no way am I implying you do not have passion for the yachting experience, just knowing it is about the experience not the boat.