@Tyler Deveraux I dont know the whole story, but coming on here and explaining your side goes a long way towards your credibility. 

Did you achieve your income goal?

I have no doubt you’ll continue to achieve great success in your investment journey.

My property manager called (I live in Denver) and told me they got it turned off pretty quickly, but a whole wall's worth of drywall was damaged. 

Not alot of confidence in any existing rentals as consistent indciators but I feel like so many homes are 1/2 rentals and don't tell the whole story.Anyone have any insight into the Cashiers/Highlands/Sapphire/Lake Toxaway markets to share? 

And the impact to housing and the economy as a whole if this path is followed?

However, in areas with little appreciation, all investment capital must come from your savings.Summarizing, a city where you can achieve and sustain financial independence must have the following characteristics:Significant and sustained population growth.A pro-business environment with a metro population >1M.Rapid and sustained appreciation.If a city doesn't meet all these requirements, achieving and maintaining financial independence will be difficult.

With enough knowledge you can make a educated decision on which approach you take.My experience:I personally don't sign up for any program who take you aside during events and try to sell packages that is just blatant sales strategy.Once you sign up there is every attempt to make you sign for their programs for bookkeeping, registered agent, LLC or corp setup fee which have ridiculous even with platinum membership.Basic standard structure they suggest to take advantage of multiple deductions can be easily achieved by proper education or work with a good firm like https://wcginc.com  who is local to you.A umbrella C-crop to manage all other LLC properties and take advantage of many tax deductions that are not available with a llc, its also used to take losses up to 100K as startup expenses and dissolve the entity after few years.Few LLC entities for investing in Real Estate, etc preferably in Wyoming or Nevada ( you can find many companies online who can do this for $150 compared to anderson $1500-$3000) , they will claim they have a secret Operating agreement which is bogus.They certainly try to take advantage of tax loopholes and claim to be smart people, my view they are just taking advantage of numbers as per their own statements.

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

Owned and wholesale residential for the last 5 years, but this is a whole new game to me.