Question 1: Should I hire a financial advisor in residency?
Most residents should be able to get along just fine with only a few hours dedicated to researching the basic financial decisions of residency:
Choosing a loan repayment plan
Choosing which insurance products to purchase and when, and
What to do with any extra income (typically a decision of whether to make extra payments on loans vs. invest).
If you don't feel comfortable making these decisions on your own and aren't interested in learning more about them yourself, choosing to hire a financial advisor may be the way to go. This also may be a good idea if you have unusually complex financial circumstances.