Captain transitioning to another yacht

Don't knock it. When I first got my ticket I chartered my 13' Boston Whaler for water skiing. Whatever it takes to be on the water making money. The sea time might be a bit of an issue though.

When you mention large yacht, I am imagining over 150'. In that case the vessel should have a full time engineer and all of those jobs you listed are the duty of the engineer, not the Captain. Most systems are pretty congruent from brand to brand and you should be able to use the items in most cases.

I run 100-150 different yachts in a year. I've run as many as 7 different ones, all unfamiliar to me on the same day even and on multiple occasions. Things work in a pretty logical order. Sure there are some nuances from boat to boat, but you usually figure those out.

Then again I was blocking a 112' Westport in at Atlantis one time, several years back and was in a lowly 58' Azimut and the Captain asked me to plot his course to Staniel Cay........no joke......how can you not figure out how to get to Staniel Cay from Paradise Island and you're running a 112' Westport.

Easy when your previous gig was captain of a dock queen.

I think you are making a bigger deal out of this than it really is. I know it may be hard for you to fathom, but there are actually motor yacht captains out there with sail experience who are more than competent and able to handle either.
I personally know a captain who jumped from a 65' sailboat to a 150' Feadship, and who then went on to run even bigger motor yachts before swallowing the anchor.

You missed the point. I didn't say a captain can't run both sail and motor. The point was that lack of experience brings a lack of opportunity. The less you know the less valuable you are.

I didn't miss the point.

One of the best pieces of advice I have heard a yacht broker give to a client is to charter first to get an idea of what your true likes and dislikes are. Try out a couple different styles of boats, and try out a couple different cruising modes.