He's constantly talking about how you need to bring the skills you are good at into your real estate investing, and find others to fill in the gaps (and your own shortcomings)It has occurred to me that one of the big ways that I can still bring value added is through my architectural skills. 

Networking is a skill you can improve on just like real estate.

I would recommend that second job be in the construction field, real estate field, or something associated with a skill set that coincides with house flipping.Then you want to learn your market and start talking to people about raising investment capital.

There are too many things that can go wrong.I would work on making as much as you can with your current skill set and save as much as possible.

I would recommend you add your comments but please know that no one with any critical thinking skills relies on that estimate - including Zillow.

Personally I believe, not all, but most people on Section 8 are of a certain socioeconomical demographic which tend to have a different set of problem solving and coping skills in life (which can be a contributing factor to destruction of property more than others) and that in and of itself is what makes me shy away from the idea of Section 8 tenants. 

Have been spending the last few months sharpening my knowledge and skills to best arm myself for when I pull the trigger on a property.

I would be working on the home full time but don't trust myself with high skilled work so there is quite a bit of subs that I hire and I have a contractor who acts as the project manager.

He hired local guys, just guys in the neighborhood with no real skills, just folks who would do the work for pretty cheap. 

As relationships are vital in this community, I’m looking to introduce myself here and see ways to connect to other investors in Chicago.