I definitely pay by the job and issue them a 1099 at the end of the year. 

So there is 100% no way I would be disclosing such a non health risk issue to the tenants. 

Quote from @Matthew Schumacher: Absolutely agree — the potential is massive.Right now, I’m exploring a few simple but powerful ways to use AI in real estate investing:Property scouting: Using AI + public data to surface areas with high permit activity, low crime, good schools — then overlaying maps to find sweet spots.Pricing analysis: Running AI models on list-to-sale ratios, DOM (days on market), and price trends to spot undervalued areas or neighborhoods heating up.Quarterly performance check-ins: Feeding financials into AI tools to flag underperformers or cash flow issues before they become a problem.Tax and financing optimization: Starting to test AI advisors to suggest tax strategies and compare loan terms — way faster than doing it manually.I’m also looking into setting up automations that pull in fresh data monthly — AI works best with up-to-date info.Totally agree — the earlier we learn and integrate, the more of an edge we’ll have.

I read this as someone using a short-term lens to focus on a long-term issue. 

Even though it's common in the area, if it's not legal, it can lead to serious issues..fines, insurance problems, or even being forced to vacate the unit.

The issue with Chicago burbs is plentiful land, so appreciation is limited.

As you begin expanding your real estate portfolio, one of the smartest moves you can make is developing a solid, forward-thinking asset protection plan.While real estate investing can be highly rewarding, it also comes with certain risks, such as lawsuits, liability claims, and unexpected creditor issues.

The issue I have seen with AirDNA is that it cannot capture live data and struggles to distinguish between a booked night and a blocked night.   

The issue is mostly that prices in these areas have gotten so high that it’s tough to make the math work without finding something off-market, making a big value-add, or going into a different niche like midterm or short-term rentals.If you’re set on traditional long-term rentals and want better cash flow, you might look at slightly smaller markets nearby, or focus on duplexes/tri-plexes where the numbers tend to look better.

While commercial wholesaling does exist, it’s far less common and often comes with more complexity and risk—including a greater likelihood of legal issues if deals aren’t structured properly.