By the way, as to how much information to put on a post here on Rootschat, the answer is always as much as possible!
This saves anybody trying to help you going over ground you have already covered, and also gives them a basis on which to research further.
What company does your information about Henry Richard's apprenticeship say he was apprenticed into?
Apprenticeships were not always with the company in which they worked.
I have lightermen who had apprenticeships with The Drapers' Company, and also a silk dyer who had an apprenticeship with The Drapers' Company and not the Dyers Company.
There is a good website called londonroll,
https://www.londonroll.org, which has information about thousands of apprenticeships. I couldn't find your Stollards. They may have been in one of the companies not covered by this site.
Do you know the distinction between watermen and lightermen?
'Watermen' carried passengers, and 'lightermen' carried goods.