STOP BEING LAZY AND FIGURE IT OUT!

What’s on your mind as you look to invest further, and is there anything specific you’re trying to figure out? 

. - You can definitely rent out for 30+ days on airbnb with no restrictions from the city of Chicago but not sure if airbnb will let you list if you don't have a license number...curious if you figure that out please share the results.Fee Simple ownership has nothing to do with what you can do with the property....It means that you own the land and the building on it outright, and you have the right to use and dispose of the property as you please.

@William SilvaRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a Class A property in Class D area, what quality of tenant will you get?

I'm trying to figure out which of these is the anomaly.

Can I reach out to HAP to figure out how much they would offer for my house? 

I want to buy however many STRs it takes to create a nice six figure income.

My employment that could pay me $X per year compared to a rental that may get me barely four figures a year in cash flow.

I can't figure this one out. ;-) 

Focus on understanding the path of progress, identifying rental properties with the most potential, learning the seasonality trends, and figuring out which upgrades will really move the needle in that area.