Dilemma 2 requires the same gravity/answer for Dilemma 1 “bankruptcy”. This has to be his biggest score; thus “a sizable fee” won’t cut it. Also, bring this closer to the home concerning whom he screws over. In its current form, it sounds like a friend of a friend situation which lessens the impact. Add connecting tissue between what he’s good at and his friend’s “business.”

Your major event “When his high-risk…” is good, also consider “risky schemes” as an alternative.

Example:
“A destitute financial advisor must choose between bankruptcy and fleecing his best friend’s firm”

Industry examples:
“A spoiled rich twentysomething must decide between true love and the vast fortune he’ll inherit if he marries a society woman whom he doesn’t love.”

“After ten years on the run from the mob, the son of a mob lawyer must choose between prison and helping the man who killed his mother.”

“A paraplegic marine dispatched to the moon Pandora on a unique mission becomes torn between following his orders and protecting the world he feels is his home.”

BTW: I don’t normally add “his, hers” pronouns in the major event as we the reader are left in the shadows concerning whom you’re talking about – until the action/goal. I always try to challenge myself to construct the logline in a way to bypass.

Take care.