But if I list it at $699,900 and it sells for $50k under asking, people think, “Wow, that property must have issues.”

I know some people in the Richmond area who may have referrals for you =) I used to manage a MTR there as well.

You're an attorney who wishes to represent people in the purchase and sale of real estate?

As far as sheriff sales most people have probaby been approached by every investor in the county possibly the country.

As a former planning commissioner the people AGAINST projects are the loudest so you want to make sure you have a good pulse on what your neighbors and the louder people at public hearings stand so you can be prepared ahead of time. 

It can be, but it should not be anything close to the reason for purchase or sale.Sloped lots require a lot of regrading to level them which is WAY more expensive than most people think.

People probably do this all the time, but skirting the law and subject to red tag if the city finds out. 

For your question, as far as I understand, the city of Binghamton doesn't allow STRs, but a lot of people do them anyway.

Intelligent people learn from other people’s mistakes.

I am sure that people who do forget their toothbrush are appreciative.