Does anyone have recommendations on some good question(s) to ask that might help me secure the deal or uncover more about why they’re selling, what price they’re looking to get, what’s “wrong” with the property, etc.

It is thinking about these sort of things and how you can best utilize those unique things that you have to work with that can lead you to a profitable niche and uncover opportunities.

However, I can still budget for a worst-case scenario if something is uncovered that wasn't anticipated or if the job takes a little longer.

You may have already uncovered this in your research, but should you choose to invest in Chicago, you will be tempted with the double digit cap rates and high returns with properties on the south side of the city.

Lastly, as you can see from the pics we uncovered the original cedar shake siding which is in excellent shape.

Researched uncovered that Accessory Dwelling Unit (ADUs) are allowed in R2.. yet seems to require a $4000 statement of occupancy.  

Your contractors may uncover some additional repairs that are needed that they might have seen when they first gave you the estimate. 

With a little extra effort, you may uncover something that would steer you away no matter how good the price.3) What do I have to offer (outside of $$$)?

Hopefully as we do our due diligence, we will uncover anything that might have been covered up, and if so, I would adjust our offer accordingly.

I know for a fact we could hire one investigator at $50,000 a year and they would uncover enough fraud to pay for the position 4x over.But, just like legalized marijuana, I disagree with it but I can't stop the machine.