They have all the skill sets needed and really seem to do a lot of transactions. 

To do landlording right, you need to know and possess the skills of the trade, not just act the part.

While he remains motivated he is unwilling to sell at a price below his comfort level.

While he remains motivated he is unwilling to sell at a price below his comfort level.

I'm and IT professional at the moment looking to pick up new skill along with a new way of life.

However in your case, since you would be forced to live in the property for a year it makes sense for you to take on more of the rehabbing (if you have the skill set to do it).Biggest issue I have with doing work myself is that it doesn’t allow for scalability.

I don't know what your specific skill set is, but I'm a bit of a geek, so I download the bulk data file from the county.  

I wouldn't DIY anything on HVAC unless you have acquired the skills to do so.

You have to acquire the skill.

Chicago cannot continue to create and keep jobs if their skilled workers don't want to live and raise a family in the City.