Second, the manager recently hired a family member to perform plumbing work on my rental after a call from the tenant - it wasn't an emergency since our usual handyman the brokerage uses cleared the backup.

In the last month, Chicago was the worst performing housing market even edging out Detroit.

Assuming 230K is accurate at sale I would have about 75K to split between a new house for family and the flipping enterprise.I hope this is not TMI but to get good advice you need to know what i am looking at.

. - Recognize there is always some measure of risk and be ok with that (by making sure you are not risking EVERYTHING and then have a just-in-case plan)- Know my own strengths and weaknesses- Overcome weaknesses by putting myself in uncomfortable situations that force me to perform or sink.

When the stress test was performed gray water came out of the Cleanout.    

Hey @Adam Bartomeo,Not unlike many who have posted in this forum, I agree that the low barrier to entry is the underlying cause for poor performance.

Are there any further steps beyond this I could or should to take to get an accurate idea of the properties true market value?

If he is purely a lender, he will be paid via interest income and his tax breaks will come from his lending business, not the performance of the property.

I'm jealous of some of the folks on BP who have the experience and are able to accurately parse out these things

This greatly reduces risk on the principal invested because, at worst, the lender owns the property and will look to maximize value by selling the property or selling the non-performing loan.