It's nice and roomy for a single older woman, but the expense is impacting our budget. 

There are a lot of ways to make this work, but there are also an equal number of ways to hurt this woman.

The larger unit would go closer to $1200 a month probably, if I could get it rehabbed (~2000 sq ft).This is a C-D class property at the moment but with some TLC could be very cute, and based on the price it seems immediately flippable for 20-30k, with the seller still getting plenty of value.What am I missing?

This is just my personal opinion and certainly there are more experienced investors here, but I think that catastrophic failure (bankruptcy) occurs when you try to get too cute with financial engineering.   

Question/advice : I have a woman that is having issues with a home that belonged to her mother.

My mother hires a second listing agent. the guy claims to be an investor and flipper, and seems a lot more knowledgeable than the last agent, but I think when an out of state woman inherits a free and clear home in an opportune location with incredibly high holding costs, everyone smells a little blood in the water... hell i would...

Sell to another investor   - If your unable to deal with her who else is going to be able to.and did you figure in : "A woman's scorn" that will kill any deal ...

I also had a woman call and ask me if I accepted a specific rental voucher and I stated I’m not aware of that voucher.

Poor woman (tenant of 7 years) called me at 2am because her basement HW tank was floating sideways & banging against the floor joists.

I am interested in a property that was owned by an elderly woman who died.