I went from barely breaking even to walking away with a very comfortable profit.This experience taught me two critical lessons:Never give up when the situation looks bleak.

I've never understood those that can't understand the critics of STRs.

All 3 parts are critical to being successful here and we’ve been doing it with todays prices, todays competition and todays interest rates.  

Hey @Mordechai Chaimovitz - It sounds like you are talking about Chicago's NW side because there are definitely tons of areas in Chicago where a 2 flat can cashflow well.I know for me buying on the nw side was critical to my personal well-being and life happiness. 

When it comes to analyzing properties, I’ve developed a specific checklist to make sure the home fits both resident needs and operational goals:Square Footage: Ideally, at least 2,000 sq. ft. to ensure enough living space for residents and staff.No Stairs or Pools: It reduces liability and keeps the home accessible for everyone (this is just my preference).Corner Lots: I love corner lots because they often provide extra parking and outdoor space—both of which are critical for families and visitors.

I listened to all the previous hearings and the general sentiment was acknowledging that STRs are critical to the area's massive tourism industry and just banning them is not wise for the local economy.

Availability and a whatever-it-takes-whenever mindset is critical too.

See Jason Alexander's character on "Shallow Hal" for a perfect example.He criticizes his friends who date attractive partners, accusing them of being shallow or warning them that "it won’t last."

I couldnt agree more though, cost is critical. 

The list goes on.For mission-critical items, you want quality, not cheap.