He now knows exactly what is going on and can use whatever influence he has to ensure that the community stays up to par and he retains the value.

I would think that whatever source that led you to IL would also have some influence on the specifics you are looking for...  

More or less equity has no influence on cash flow.

You will have local trends, new starts, employment, gentrification, social influences, public amenities as well as commercial activities.

Two books that have had the biggest influence on my real estate career and financial goals:Millionaire Real Estate Investor - Helped me shape my RE strategy.Think and Grow Rich - Helped me get money minded.

Kyne How to Win Friends & Influence People by Dale Carnegie      Real Estateby Ken McElroy.

We use instagram and other social media platforms, in tandem with influencers, to drive traffic to our website.

So if you have connections to influencers, television, athletes, producers, and musicians that could make use of a higher-end property consistently, you may have an advantage.

When you're looking for comps and value, how much of an influence is there between proximity to the house you're looking at, the property specs, and what you can do to it? 

It's pretty bad that when I want to search on BP that I have to go to Google to do it....Plus...There is a ton of fantastic blog content that needs to be way better organized and indexed so that the many great influencers on BP, like @Russell Brazil , @JD Martin , and Alex can help steer new members to the already existing fantastic content.