Some focus purely on numbers, while others look at long-term value, location trends, or creative financing strategies.For those of you investing in Chicago (or similar markets), whats your mindset when evaluating off-market opportunities?

This will be my first pure investment purchase, my experience up to now has involved house hacking.

I've had my GC run through the property and he did not discover any leaks, so I'm purely confused why I'm seeing this massive increase.

However, if you're leaning more toward **purely investment properties** and have the flexibility to dive into the numbers, I would recommend looking at the **South Side of Chicago**.

If you are seeking purely an investment property, you will want to consider additional markets.

So someone who is looking purely to maximize potential return (and has unlimited time) is unlikely to find this a good fit.

And is it purely an investment or also something for you to live in?

There are still some good markets that will provide cashflow but you'll need to have realistic expectations when investing purely for cashflow. 

Also, if the role is purely commission-based, would I need to maintain a parallel career to make ends meet?

If you take a newborn who has been feeding on formula and give them puree veggies they will think this is the best thing in the universe but that's because they don't know any better.