One thing that happened back then its the rise of all this private money..

@Michael Smythe - Agreed it is all basic stuff to you and I in the field of PM.

But as of the last 6 or so months I seem to be losing direction.

The answer is that if the lender that's doing the hard money loan is only funding the purchase and not the rehab, they then have less oversight of the project since they're not doing the draws, and thus not seeing the progress of the project and having control of the funds or draws from the rehab to make sure the project is progressing.

You need a reserve to handle unexpected costs, particularly during the first 1-2 years of ownership and learning how to manage the property. 

Illinois is tenant friendly state.

You'll be in the middle of the overall upper east side apartment market. 1 or 2 beds 1 or 2 baths in a nice and safe building.

He still buys at a discount regardless of the strategy.

You can ask (if it's not obvious) what the nature of the disability is and what task(s) the dog has been trained to perform.

Then I would either go to your GC with the info, or go directly to your subs (licensed electrician etc.) with the info.