Learn to walk away and failing.  

Literally as I am typing this on my phone, I just watched some lady walk from across the street with a chair to sit in front of my building.

Or should I just walk away and concentrate on renting the one property we have under contract?

The only caution I would say is not on the insurance side but on the sales side, if I walked up to a property and saw a bunch of patches on a roof it would be a red flag to me.  

An exception for water may be a duplex situation where there might be one meter for two units and thus the landlord MIGHT keep the water in their name and bill the tenants.Cost of trash pickup is dependent on the particular area (we pay for it as it is added to your yearly taxes).Utility responsibilities are discussed with applicants during their walk through. 

It's all about the numbers and I would guess that if you partner on here the person will also be knowledgeable enough to walk you through any inconsistencies you may have in your numbers. 

Most walk because they cannot see the opportunity.

This is where if you are gonna be a salesman,you need to use your powers of persuasion.Find their pressure points and emphasize you are there to alleviate those pressures.Take control of the negotiations by gently reminding them that you want to buy but can move on to the next deal at anytime.You have to make them worry that if they don't cooperate and comply with your contingencies,you will walk on them.Why are they selling?

If, at the end of the lease (or on month to month), then we can talk about walking the property & deducting what's necessary from the security deposit, then starting over with new sec dep and new lease with just her on lease.

I'm considering walking away from this deal but the property is about due for a price drop based on days on the market so I want to fully explore my options before we walk away from it.