To name a few factors: your time commitment, ability to focus on marketing & sales, your network...As a current business owner, you may already have a pretty good starting point.Most agents close 1-2 deals their first year (if any)...

But any company that properly creates and maintains a liquidity sleeve like I described above, is going to be able to honor its commitments. 

Please at all costs do not commit mortgage fraud based on the advice of someone who will deny they ever spoke to you about any such thing if all hell breaks loose

In the meantime, wholesaling could be a great way to make some cash, learn the ropes, and build connections without a huge financial commitment.

Premium increases are rippling through the market; the state is also always going to be financially strapped/high tax due to union pension commitments from past generations and the high tax, high services nature of Chicago.I'd highly recommend getting on a plane and driving around before you buy anything there. 

Additionally, make a commitment today to at least spend a few hours a day learning about real estate investing.

However, like others here, I don't like the longer term commitment especially when getting in at this economic cycle.   

The key to navigating this market successfully is to stay vigilant and committed to this niche for the long term.

With a CC you don’t have to worry about scaring customers away and you also protect yourself.Also, if I were looking to commit a violent crime, my first person I’d target is someone with a visible firearm.

Balancing job and investing stress requires prioritizing properties and strategies that align with risk tolerance and time commitment.