[BeetleB]

A very common one: You have a debt to pay off (typically mortgage). Should you put all your extra money to pay it off early or should you pay the minimum and invest the rest?

As another commenter pointed out: Most investments involve this. In the RE circles you often have the same dilemma: Buy a house for rental in a LCOL area where you get (mostly) guaranteed net income, or buy in a place like California where the rent income won't cover all the expenses, but you feel you can pay the difference and rely on profiting off the hoped appreciation.

Insurance is also a good example someone else pointed out.

Even: Get a guaranteed low paying job as a relatively unskilled worker, or get into deep debt to go into medical school, do a residency, and earn a lot. The latter can have significant risk: Some people don't do well enough to get a residency. Others get the residency but don't have what it takes to complete it. In both cases you're left with a huge amount of debt.