In your case going to a fifth unit as noted above could actually reduce the value, so I'd be cautious of that since that materially degrades their collateral.

It’s been a grind, but I’ve built some great relationships and have been able to lock up some strong opportunities because of for my investors. 

@Jennie Berger gave you the whole kit & caboodle on Chicago zoning so I don't have a ton to ad, however, I'd highly encourage you to engage an architect like @Samuel Pavlovcik or @Prashanth Mahakali, both are awesome local Chicago resources.

Final Water Quality Plan.10.

We’re currently using it for multi-family properties in a few core markets.While redIQ is a much more sophisticated tool that focuses on properties with over 50 units, our system is perfect for properties up to 50 units, providing an efficient solution for managing lead intake and financial analysis without the complexity of larger systems.Here’s how it works:Lead Intake & Processing: Automatically processes broker emails and key documents (OMs, Rent Rolls, T12s, etc.).Quick Review: Evaluates leads based on key metrics like IRR, price per unit, and more.Detailed Analysis: Extracts data from documents, evaluates financials, and identifies additional income sources.Market Research Integration: Automates checks on flood zones, demographics, school quality, etc.Deal Tracking: Uses Google Sheets to visually organize lead data—while not a full database system, it provides a simple and efficient way to store and track deals without the need for a full-fledged database like MongoDB.Financial Analysis: Built-in underwriting and financial modeling with automated reports.In addition to ZCG, I also own a portfolio of properties.

ADU's over 750sf receive reduced impact fees (25% of SFR charge).

Selling at FMV avoids the gift tax but provides your child with a higher tax basis, reducing their future capital gains liability.A better strategy for selling below FMV is to sell the house at FMV on an installment note, then forgive interest and principal annually up to the gift tax exclusion amount.

3) What neighborhoods would you recommend in this price range if I'm targeting high quality tenants?

Another option is a Tenancy-In-Common (TIC) structure, where ownership is split between you and the LLC, allowing compliance with 1031 rules while securing financing.This post does not create a CPA-Client relationship.

These properties are generally in high demand, but on a positive there will be drastically less new inventory of competing rental properties.