For some, a smaller market with lower property costs may provide greater financial flexibility, while others might prioritize high-demand cities for quicker tenant turnover.

Other than that, the city is largely residential with many jobs focused around providing for those residential needs such as the service industry sector, home repair, construction, etc.

I'm generally a proponent for alternative lenders if they can provide better leverage or if they are needed due to time constraints.

I don't want to work all my life, and have nothing to show for it other than dying with a bigger bank account than most people.Having a modest level of financial independence provides, perhaps, the least amount of clarity compared to either having non at all or being super wealthy. 

Quote from @Stuart Udis: @Satyajeet Dodia  You are the latest to pay for their alarmist asset protection service provider's  holiday vacations and children's college funds.

The lifestyle question is one that you must determine, then narrow down what parts of Chicago provide you with that lifestyle, then we can really answer the question- How is the market doing in those specific neighborhoods?

Though I have not personally contributed to these investments for tax credits, I have personally seen these investments in action and these investments can help provide more supply of housing and development that would otherwise not be there.

Could anyone provide guidance on how to obtain the contact information of an underperforming host on Airbnb?

@Jaren Woeppel I own a management company that focuses almost exclusively on the management side for revenue and has right at 700 doors under management.

They have a formula that works and provides them the rate of return that makes it worth it so, don't feel like you'll just negotiate them out of their shoes like you're Trump.