#706: When the numbers look straightforward—but the rules, timing, and future are uncertain—how do you decide what to do next?

• KJ has $90,000 in student loans, a recent inheritance, and a lot of uncertainty around changing repayment policies, and is trying to decide whether to pay down debt now or hold onto cash in case future payments become unaffordable.
  

• Anonymous (let’s call her Andrea)  is about seven years away from retirement with $1.9 million saved and is thinking about sequence of returns risk, and is wondering whether working part-time could help protect against a poorly timed market downturn or simply delay the risk.

• Anonymous (let’s call him Andrew Ryan)  is a retired homeowner in their early 70s who recently bought a second home to be closer to family and is planning to rent it out part of the year, and is wondering how to structure it and how taxes work for a property that’s both personal and income-producing.

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