Real estate investment news you can use!

December 2025

MESSAGE FROM THE BOARD

From House Hacking to Happy Tenants: A 25-Year Real Estate Journey

I got into real estate investing 25 years ago with a simple idea: buy a property that could help pay for itself.

Here’s how it all unfolded—and how we’re continuing the journey today.

The Beginning: Our First Two-Flat

Bought a two-flat in an up-and-coming neighborhood.
Lived in the large three-bedroom, two-floor unit.
Rented the smaller two-bedroom, one-bath unit below us.
Rented to couples or singles with good credit and references.
Rental income helped cover the mortgage, while we built equity in a rising market.

We loved the vibrant neighborhood but eventually realized we needed more space—a yard and a driveway—to start a family.

The Next Step: Moving While Renting

Found a home in another up-and-coming area that fit our family needs.
Kept renting out the duplex unit.
Rental income covered the two-flat mortgage and half of the new home’s mortgage.
This strategy allowed us to move into a larger home without overextending financially.

Fast Forward 25 Years: Empty-Nesters and New Plans

Our single-family home will soon be rented to women over 55 who want to share space and live together.

Provides steady income and a sense of community for tenants.

House Hacking, Round Two

We’re planning to dive back into house hacking with a multi-unit property:

Looking for at least a two-unit property that needs some work.
Plan to live in the unit for a year to maximize tax benefits while renovating.
Rent out the first unit once it’s upgraded, then move into the second unit and repeat the process.

Goal: increase rental value, create quality housing, and continue building wealth.

Lessons Learned Along the Way

House hacking is a powerful tool for reducing living costs and building equity.
Rental income can help you move up in life without taking on unsustainable debt.
Real estate investing is both financial strategy and personal journey—adaptability is key.

Even decades later, the right strategy can continue to provide both income and lifestyle benefits.

Real estate has allowed us to live in neighborhoods we love, support our family goals, and continue creating opportunities for future investments. Whether you’re a first-time investor or looking to scale your portfolio, strategic house hacking can make a real difference.

Pk Kleinert
Chicago Area Real Estate Investors Association - Programming Director

Upcoming Events

CAREIA

Board of Directors

CAREIA Monthly General Meeting

Monday, December 8, 2025 @ 7:00 p.m.
Networking starts at 6:45 p.m.
Hyatt of Lisle • 1400 Corporetum Drive, Lisle

Topic: Mindset and Pre-Foreclosures

Key Note Speaker: Nita Patel

https://www.careia.org/event-6423989

Short Term Rental Sub Group Meeting

Monday, December 15, 2025 @ 7 p.m.

Portillo's Hot Dogs, 531 N. Randall Rd., Batavia, IL 60510

A FREE Member & Non-member Event

Anyone who has an interest in investing in short or mid-term rentals are invited to attend our monthly STR sub group meeting. Each month we will have an open forum to discuss all things short term rentals.

https://www.careia.org/event-6423985

Real Estate Networking Night

Monday, December 22, 2025 @ 6:30 p.m.

Portillo's Hot Dogs, 235 E. North Avenue, Glendale Heights, IL 60139

A FREE Member & Non-member Event

https://www.careia.org/event-6423983

Cash Flow Game Night (Members Only Event)

Wednesday, January 7, 2026 @ 7:00 p.m.
McDonald's off Highland Avenue
1 Yorktown Shopping Center, Lombard

https://www.careia.org/event-6466734

CAREIA Monthly General Meeting

Monday, January 12, 2026 @ 7:00 p.m.
Networking starts at 6:45 p.m.
Hyatt of Lisle • 1400 Corporetum Drive, Lisle

Topic: TBD

Key Note Speaker: TBD

https://www.careia.org/event-6395197

Short Term Rental Sub Group Meeting

Monday, January 19, 2026 @ 7 p.m.

Portillo's Hot Dogs, 531 N. Randall Rd., Batavia, IL 60510

A FREE Member & Non-member Event

https://www.careia.org/event-6466735

Real Estate Networking Night

Monday, January 26, 2026 @ 6:30 p.m.

Portillo's Hot Dogs, 235 E. North Avenue, Glendale Heights, IL 60139

A FREE Member & Non-member Event

https://www.careia.org/event-6466736

President: Pete Gordon

Vice President: Steven Bell

Secretary: Rob Hayes

Treasurer: Vanessa Krynen

Librarian: Dwayne Denzinger

Programing: PK Kleinert

Vendor: Iva Norris

Newsletter: Belinda Moore

Publicity: Mary Ann Skweres

Membership: Danny Galvez

Tech Support: Keith Jablonowski

__________________

Our mission

To support and
promote local real estate investors
though networking, education, support, leadership on
legislative issues,
and promoting professionalism
and standards of excellence in the
real estate
investing industry.

__________________

WORDS OF WISDOM

"If you can find a path with no obstacles, it probably doesn't lead anywhere.” – John Wooden

Library Book of the Month

Probate Real Estate Investing: The Ultimate Guide to Buying and Selling Probate Real Estate

Jeff Leighton

Learn how to find great real estate deals that most people don't even know exist.

In this book, you will discover...

How to start doing probate deals ASAP, even if you know nothing about the probate process.
How to find any probate list and even outsource the list building for under $5 an hour.
Learn 5 different marketing strategies that myself and other investors have used to consistently find deals.
How to avoid common probate investing mistakes.
Learn multiple exit strategies for probate deals so that you can maximize every lead.
And much, much more...

The Ultimate Guide To Buying and Selling Probate real estate is for any investor or real estate agent who is looking to get more out of their business utilizing a special niche (probate) that has significantly less competition than any other niche of real estate.

This book will help you get started in the probate world or if you have experience already, can take your business to the next level with proven strategies from a real estate investor.

To check out materials:

Only members can borrow materials
Review inventory here: https://www.careia.org/LibaryList
Fill out CAREIA Library request form
Receive materials at the next General Meeting
Materials are due back in one month
Note. If materials are not returned, member is responsible for paying cost of materials for replacement.

National REIA Benefits

Members of CAREIA can register at National Real Estate Investors Association (National REIA) https://nationalreia.org. and learn about the negotiated group discounts from National vendors. Login CAREIA website https://www.careia.org and go to Account -> Members Only: National REIA for more details.