Cost segregation studies identify assets for accelerated depreciation and correct the depreciation according to MACRS. 

One was on a duplex we had removed multiple layers of old linoleum from and staged on the front porch to be hauled to our dumpster and the other was that house fire I wrote about on another post.In both cases I was able to immediately call the city inspector, get an understanding of what the issue is and identify that I "work in Toledo, invest in Toledo, pay taxes in Toledo, believe in building a better Toledo" and give them a specific time when the issue will be resolved.

This assumes that these are not retirement funds that you would incur penalties and taxes to access.HOWEVER, I would make a detailed budget and identify where I could squeeze extra money out of your cash flow from employment to take down this debt first.  

Including equity, cash flow, appreciation down the road?

What other key indicators you need to identify when looking to invest in an emerging market.

What happens if she starts abusing this down the road?

The long holding period is not due to the applicant either - so to hold their money during that HOA approval is probably a practice I would avoid; I would try to identify what goes into the HOA approval process and add that to my INITIAL approval process so that I know there is a high likelihood of HOA approval.Now, why was the notion of "getting a holding deposit" introduced (not by you, but in general)?

Who do I consult with on the rules of the road?

I think this property will be an easy sell down the road and will still be in great shape compared to others on the market.

You go with another agent you pay the agent a commission on the properties he identified.