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.

No shortage of renters in the rental pool, but how does the actual housing market do?

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. 

However, +5 units do come with more things that I need to learn about before just jumping in.What I'm running across are for-sale owned by investors that have several duplexes.To hone my skills, I am doing analysis from what I learned about deal analysis, thanks BP community, to see what I come up with.

At the moment I don't have any technical skills but I am looking to get better.  

On the sheet I also ask if there are suggestions for the place and whether they have a skill set that could aid us in accomplishing some of the suggestions or help with the place in general.  

This naturally means that system analysis, integration, custom development, and maintenance skills are part of my toolkit.