One's tolerance--and desire--to navigate some of these issues stands to vary greatly based on whether it's a true labor of love or something you hope to hire out free of worries.With the cabin--before diving too deep into financial calculations--it would be good to get a clear assessment of its condition.

It all comes down to getting the right mix of index funds for your time horizon and risk tolerance; you don’t have to pay a financial advisor crazy amounts of money to do that; in fact you could just invest in a lifestyle fund that automatically rebalanced in the time horizon you are looking at.As for an advisor who can do both.  

The answer depends on so many factors including but not limited to: age, risk tolerance, job type, job income, job stability, long-term goals, education, type of market you will invest in, current savings rate, cash reserves, etc, etc. 

You should consult with your lawyer and make that decision based on their advice and your tolerance for risk.3 - I am not a huge fan of paying off properties especially if I just have one.

Investor sentiment, in turn, is what sets prevailing prices (i.e. prices that investors are willing to pay based on their required ROR and risk tolerance) which, in turn, translate to a certain cap rate.

I'm doubting I could actually successfully evict them for noncompliance, and it would just become a mess, it's exactly the kind of conflict in which NJ is tenant friendly, while nonpayment has zero tolerance.  

@Jared Baker Based on your research and your current risk tolerance/situation you feel comfortable buying a single family.

You have to know your own personal tolerance for a worst case scenario. 

Is this a risk that is taken depending on the investor's tolerance or is this just never a wise decision?  

She has been there for many years, her lease expired three years ago, and up until recently she has been tolerable.