That can work if that is your strategy. 

Much appreciated,J I know @Jonathan Klemm has operated a STR in Chicago and I believe you are correct about the occupancy rules.Like @Michael Baum said considering the mid-term rental strategy (30-90 days) may be a good strategy to get around STR rules.

Everyone has a different strategy so reach out to as many professionals and investors you can for their feedback.   

Are you trying to do a rent-by-room strategy?

I'm reaching out to gather some insights and feedback on a strategy I'm considering for my first investment property.

What other strategies in real estate investing should I divert my energy towards and look at? 

Roosevelt: “The best customer of American industry is the well paid worker.”

Hello @Hector MejiaFirst thing you will need to know is, what is your investment strategy.

Do you plan to repeat this strategy consistently in the future?

Usually it's the customer changing their mind about something.