@Sean MacDonaldI think you summed it up in your observation of your clients, it's very typical here in the valley that the number of transactions will decline right before an election and then those buyers just like your clients will get back in and the number of transactions will pick back up in the months following the election.

Not specific to OP but I constantly observe the pressure investors face to buy real estate.

@Melanie Baldridge, I agree with your observation.  

From what I observed there's bigger income to be made with due diligence to find that property, but with big income can come big risks if you're not careful which scares me so much tbh.

As I've observed, after a down period, the market tends to recover and show growth for approximately three years.Timing the market is a skill every real estate investor should develop.

Even though the distance would be a lot farther to travel than initially investing in another Chicago neighborhood, I know the tenant laws are a lot more relaxed out in the suburbs, the average price of property is much lower, and it just feels like a smoother entry point than a large city in general.I'm very interested in multi-family properties to begin my real estate journey and have worked on putting a team together, so I am getting closer to actually acting, not just observing.

Just my observation.

My own observation leads me to believe that a large part of the buyer agent’s time budget gets spent on showing houses and transportation to and from those houses.

The fact that they have received so much insight by being able to watch and observe you will open up a whole lot of opportunities for them if they so choose. 

Most municipalities have different mix-use categories which dictate the precise commercial use that's allowed.A few additional observations on mix-use assets and how I approach them (1) they are generally more difficult to finance than multi-family assets so expect lower leverage terms even if the property performs just as well if not better than a multi-family property and therefore price this into your acquisition (2) I focus on mix-use assets where at least 80% of the income is generated through the residential component.