He said yes but still insisted he wanted to pay, I rejected payment, however he has paid extra on every job since then which I suspect to be making up for not paying then.In all this time I repeatedly ask him if I can work for him for free and learn, my downtime is winter, he always says no somewhat informally and instead gives me a gem of a piece of advice and then a new step.

If you ended on a round number it is uncommon but not out of the question, I suspect it is a coincidence, because if they do that often someone will catch on.

I suspect they'll appeal the ruling.

The $8,700 included a couple of items that involved demolition and restoration of concrete slab that had a pipe buried between the walls that was initially suspected as the cause of the leak, to the amount of $500. 

Since this particular property is in a popular vacation spot in Ohio and setup like town houses, I suspect there may be a HOA. 

I would suspect this lot is carved in such a way that building is not prohibited, it would just be economically difficult. 

I'm looking in Lincoln Park/LakeView, Bucktown/Wicker Park/Logan Square, Little Italy, Gold Coast/Old Town (open to suggestions of other neighborhoods to consider) I'm trying to understand what properties are "a good buy" and what are overpriced but I am struggling to identify appropriate benchmarks: I keep reading about the 2% rule as method to identify "good deals" but I can't seem to find properties that meet this requirement (and I kind of suspect that this is not realistic in Chi).... and I am not even sure what rule of thumb to use to evaluate properties for AirBnB.Anyone willing to share wisdom or - for people owning a similar property - willing to share approximate numbers?

I suspect since it was owner occupied that you have low cash into the deal and low interest rate.

I suspect that you met their criteria, but they'd prefer to have someone else for some reason.

She seemed to be doing a decent job, but there has been suspect advice along the way.