If property owners are not using an architect at this stage, are they simply making a submission based on an educated guess as to how much it will cost to provide the space needed?   

@Harsh PatelI would pause on OOS investing Unless  you have plans to scale up to five or ten properties in a two year period.

Since you are just getting started, I would  invest some time in education.

Hey Everybody, Has anyone taken the broker license course through http://www.illinoisrealtors.org/education/ or https://www.realestateexpress.com/real-estate-license/illinois/.

I would focus my time educating myself in the investment strategy you are going to execute as an investor.

As long as the Tenant is on a month to month, and proper notice is given, a rental rate increase would be an acceptable ask.Just verify that the appropriate notice period still falls within your escrow. 

I'm in favor of a short term lease (they can pick the period, but then you set the price) or another 12-month term with the standard rental rate.  

We've speculated that the offers may have been rejected because of the due diligence period being 7+ days, or perhaps being contingent on inspection, but have received no feedback from the agents as to the true cause. 

I have listened to the podcasts, read blogs, followed forums to help educate myself on the market trends.

That is the only time I have ever heard of a required waiting period.