[susan53]

Now for the second group :

a) swimmingly : this is very colloquial and would only be used in very informal style, most likely in spoken discourse though a very informal written message to a friend is possible. However, it only collocates with the verb go to form a fixed expression : to go swimmingly = to proceed without problems - eg : We were worried that the preparations for the conference hadn't been thorough enough, but it all went swimmingly. It can't be used with any other verb or in any other expression. It sounds to me slightly old-fashioned though, and rather "upper class" - like something a character in a Scott Fitzgerald novel might say.

b) prosperously : You can't put this together with the expression make money, because it means the same thing. If you make money it means you are prosperous. It would be like saying "He lied untruthfully" There is no other way to lie.

c) effortlessly is OK - but notice that it has a precise meaning : without difficulty. If that's what you want to say, fine. But if you're just trying to say that he made a lot of money, then you need a different expression. Depending on the style of the discourse, I'd suggest :

His long business experience and excellent marketing strategies helped him make a large amount of money. (Neutral)

He was making money hand over fist. (Informal)

Your real problem in both these groups of sentences is that you are trying to "force" an adverb into an expression which wouldn't normally use one. That's why you're having so much difficulty.