After discussing their goals, we realized they would like to maximize the property's value while also including me in the process, given my background in general contracting.

I am admittedly a newb in the process of getting all of this set up for my first rental (so correct me if I'm wrong) as well but I have some IL-specific perspective to offer: From what I have read, as of 1 Jan 2024 in IL, landlords cannot exclusively accept EFT payment of rents (includes Venmo, Zelle, etc.) for leases starting on or after that date.

Your calculations should include utililies and repairs, legals, snow removal, etc.

Answer: yes, we're less than a 5-minute walk to the lift but you need to be skiing at blue+.

I reviewed the SB9 legislation, and it states that properties occupied by a tenant in the last 3 years are excluded from SB9 but only if the project includes demolition or altering more than 25% of the exterior structural wall.

There are a bunch of great investors who are more than happy to share and network (including myself). 

Main benefits to this strategy include:- Low down payment options (as low as 3-5%)- Acquisition experience- Property management experienceThe NYC metro area has nearly 2,000 available 2-4 unit listings on the market.Other new investors consider the BRRRR Strategy.All the best to you on your journey!

Luckily, I did not include this unit in my underwriting when purchasing, so the survival of this property is not contingent on this situation.Continuing to optimize for management of the building when I move out, like moving everyone to online rent payments or adding remote accessible security cameras.Exploring opportunities to expand my portfolio—I've begun my hunt for my next 3 to 4-unit building to house hack, ideally in Lake View, North Center, or Ravenswood.This year taught me that real estate investing isn’t easy, but it’s undoubtedly worth it.

If done right most of these gains are tax-free- $40K in equity capture (profit) with $20K out of pocket and 13% cash on cash thereafter (300%+ returns)- $24K of equity capture with $32K out of pocket and 36% cash on cash returns thereafter (75%+ returns)- $41K of equity capture with $27K out of pocket and 12% cash on cash returns thereafter (150%+ returns)None of the above numbers include loan pay-down or appreciation. 

Here's an article with FAQs including the cost of a study.