You'll likely have some utilities costs during vacancy, home cleaning, carpet cleaning, landscaping, etc until the home is rented.  

Howdy @Chris NordellaThe first thing I see is you have Vacancy and Maintenance together.  

Your chances of someone buying it is 100 % better if it is cash flowing opposed to vacant & them trying to fill the vacancy once they purchase said property.

If you don't like leasing fees or a percentage of rent, work out a bonus structure for keeping vacancy under a certain threshold across your portfolio or escalating bonuses for tenants that renew multiple times.

Extended vacancies only really happen due to bad management or renovation.

Taxes, insurance, capex, property management, vacancies, grass, snow, water and mortgage have me coming in at ~366$ cashflow a month at the 95k asking price.

In particular, I'm curious to know if there's a particular set of circumstances or mitigation strategies that could make the increased risks (vacancy, credit, property crime/damage, etc.) worth it. 

What is Vacancy rate for the area?

HUD/ local section 8 or are tenants able to qualify & pay- average vacancy rate & average time to fill apartment Sorry for the laundry list, hopefully someone experienced in these and other D areas can enlighten me.

That could be a powerful leverage point.From a business negotiation angle, you might let your agent or the seller--if a FSBO-- politely know the vacancy will expedite the closing and give you confidence to sign on the dotted line.