Anyone investing in small multi family in Chicago?

The houses in the neighborhood are actually really nice.

Hello, we sold a house and during the final walkthrough the buyers noticed the well pump leaking.

Are you seeking helocs on investment property or primary residences.?

RE Pro Status supercharges this.If you or your spouse are an RE Pro, your LP investments can lead to depreciation offsetting both passive and active income.If you are not an RE Pro, the losses due to depreciation can only be used to offset passive income—such as income from other rental properties or other passive investments.

Also, if I was to take out $50k from the first property to put a 25% down payment on the second house, would there be an easy way to tap into the rest of the equity in the first house if I wanted to take another $50k to buy another house in the future? 

Or would I have to buy it as an investment property with 20-25% down? 

And no, that wasn't the minimum charge to go out to the house)

Start by reading the Ultimate Real Estate Investing Guide: https://www.biggerpockets.com/guides/ultimate-real-estate-investing-guide/introduction2.

so in 2018 i invested to one fund that's offering regular decent cashflows.