I own 4 STRs in Indy and have looked into the Nashville, IN market.

Insurance : This area of consideration deserves its own deep dive so we’ll briefly highlight key concerns. - The underinsured.

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.

It’s definitely exciting to see suburban Chicago getting recognition as a hot rental market—it’s something I’ve noticed in my own experience as well.

or options 3, 4 and 5 don't supply washer and dryers and either the tenant provides their own, rent appliances or goes to community laundramat.

Do you own your primary residence?

E Equity, how much of the home will you own on day one.  

However, as the saying goes, while everyone is entitled to their own opinion, nobody is entitled to their own facts (as there is only one set of facts). 

Quote from @Keegan Darby: Hi BP - I’m seeking advice on a property I own. 

Long-distance investing can definitely be a good way to find better cash flow, but it comes with its own challenges, especially for a first-time investor.