Instead of diving straight into business, I'd chat with property owners about their goals and challenges.

It's great to keep learning on your own (I'd recommend the Straight Up Chicago Investor Podcast which is specific to the area), but Chicago has a very vibrant investor community and you can learn so much from others.

Wait, let me get this straight... 

Turbo tenant is the only one I actually pay for straight away - $99 for the year.

If you're effectively filling orders for a legit buyer then wholesaling to them becomes a straightforward matter.As was already mentioned, however, you may be best served not focusing on trying to wholesale and instead buying the land at a steep discount and going straight to the retail market.

This should be a relatively easy and straight forward loan, @Christine Barker.

I offered cash, about $10k below asking...pretty straight forward.

The key benefit to a Dutch repayment schedule is that they are often easier to find, the approval requirements are lenient, they tend to close quickly, and the calculation is very straight forward easy to keep up with.

Straight to the point and accurate. 

Would love to get this all straight so I can start adjusting my strategy confidently!