The ends either justify the means or they do not. If you start piling conditions on the question, there is no rule involved.

For each person, conditions depend on their own personal beliefs. That renders the question unanswerable.

It's a simple question. The answer is either "yes" or "no." There is no maybe as a possibility.

...this would be one of the pages in the workbook that has a note at bottom saying that the solution is left as an exercise.

It's a good idea to have an opinion ahead on what means are within your moral standards and which aren't.

IMO, it's better to ask "should I" before asking "can I". Hindsight has a way of degrading one's original intentions.
OTOH, if the ends can't justify the means, what can?

but my not caring if a man whose job it is to find new and more creative ways to deny necessary health care to people is dead is OK.

When that orange man dies, I also won't care.

And must be evaluated that way. In general no, but maybe sometimes.