would love some commentary from peer cities in the midwest especially property managers or STR managers.

Find the manager first, then find the properties. 

If you prefer to maintain privacy and don’t want your tenants to know you are the property owner, I often recommend a two-entity strategy.

We are working with our property manager getting everything ready to go- we are just a few weeks out from going live (fingers crossed).

- I understand that properties go to auction, but what’s the process like from start to finish? 

This property has been flipped, and rent exceeded the one percent rule.

In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

It's more important than doing individual property analysis, because when you do a proper market analysis, you are analyzing ALL of the properties in any market(s) at the same time.Now, one of the analysis "pitfalls" is not understanding what defines a market, or more importantly, a Micro-market.Another problem is focusing on one strategy, and trying to fit each market/property. 

I’m a real estate broker, Investor, and property manager in Lee County.

Quote from @Judah Zuckerman: why don't you try LoopNet or crexi they have all types of property's' They really only have 1 type of property.......overpriced.