The current tenant was already in place when I purchased the building, and their lease is set to expire in a few months.

I called the zoning department and they are telling me this is a Mixed use building (N zone).

With a 4-unit building, that’s a very high customer concentration.

Every property will bring its own lessons, so just be ready to roll with the punches and use what you learn to make your next investment even better.

that doesn't seem ideal - i think people should build up a track record before borrowing private money and putting it at risk.  

I got my GC license a couple years ago so I could build houses myself as I was sick of dealing with contractors.I've hired plenty of contractors that were not licensed/insured and it went fine.

But it’s clear you’re a smart investor who knows the long-term benefits real estate can bring.I keep reminding myself why I stick with real estate: you can make money every month in four different ways:Cash Flow – Passive income to live on.Appreciation – Long-term property value growth.Depreciation – Tax benefits that reduce your taxable income.Tenants Paying Down the Mortgage – Even if you’re paid off now, this is one of the biggest wealth-building tools for leveraged properties.It sounds like your main struggle is the stress of active management—and trust me, you’re not alone.

That 36% rent increase while keeping happy tenants shows how smart and intentional you are about building relationships, not just cash flow. 

A community of growth oriented, abundance mindset, go-giver individuals with a BARE MINIMUM commitment to become financially free through real estate investing.We focus on providing education and building networks to help every member solve their cash-flow freedom equation, so they can have the time-freedom needed to follow their passions, make a lasting impact and even change the world!

Then to build your teamBut most of all for my advice, I'd be looking at Milwaukee 1000% before Chicago!