Be sure that whatever structure you decide is best for you that you also understand how your business will operate to ensure that the structure or corporate veil is preserved.

With no experience in STRs yet, I’d say give yourself the best chance to win by ensuring you have enough capital to buy and invest in a property that guests will want to pay you more than everyone else for because of those decisions you made on timing and acquisition.my two cents!

I haven't take the time to look at the real data on what's going on with the rental market in Chicago but our system has blown up with inquiries.  

If you've spent all of your money and have no way to keep marketing to whatever list you've used and can't buy more data, you are all done for now.

Depends on the property management company and ownership.Larger property managers will have a "standardized" CoA (we do that for 1000+ units across 5 properties we own and operate), HOWEVER, the person entering the data (typically the onsite PM) still needs to make sure they use the correct accounts for entry....and then the Regional Managers should check the PM's work regularly.

You can see visitation data, including how the last recession affected tourism (spoiler: not much) here: https://irma.nps.gov/STATS/SSRSReports/Park%20Specific%20Reports/Annual%20Park%20Recreation%20Visitation%20Graph%20(1904%20-%20Last%20Calendar%20Year)?

I intend on managing the property myself under the LLC, but want to ensure I dot my I's and cross my T's by hiring an accountant.

What would be some ways of ensuring a broker or realtor is investor friendly?

Their agent did them a disservice or they all knew what was going to happen (looking for the 1 in a million buyer, not caring about the data or neighborhood to put up that kind of money) just to "test it"So ask yourself this question...are you testing, or are you selling? 

Im in houston texas and would like to know what performance metrics should I seek in a 1 to 4 unit home to ensure Ill get approved for another loan year after year?