Vendor Portal
Today we’re joined by Nate Fernandez, also known as "Real Estate Nate"—a full-time W2 employee, father of three, CRM consultant, and Chicago landlord with over 20 units. If you think you’re too busy to build a real estate portfolio in Chicago, this episode will absolutely change your mindset.
From balancing family life to building systems that scale, Nate walks us through how he created a cash-flowing Chicago portfolio without quitting his job. Whether you're just starting out or looking to scale up while keeping your W2 income, Nate shares actionable strategies every Chicago property manager and investor should hear.
We talk about the Proviso Corridor—a lesser-known area near Hillside, Bellwood, and Broadview—and why it’s a hot spot for cash-flowing multifamily properties. Nate shares how he got started in Broadview with a four-unit property, how he leveraged HELOCs, 401k loans, and family partnerships to scale, and why he’s still bullish on these West Suburbs.
This episode is similar to a masterclass on resourcefulness, risk management, and systems. From selecting the right property management tools to leveraging community banks and partnerships, Nate shows us that you can build a serious portfolio without sacrificing your lifestyle. If you're a W2 worker wondering how to make real estate investing in Chicago work for you, this is the blueprint.
Nate is living proof that with the right systems, team, and mindset, you can stack units while raising a family, running a business, and still hitting the gym. If you enjoy the episode, leave a review, subscribe, and share it with someone juggling their W2 and real estate dreams.
Questions We Answer in This Show
Q: Can you build a Chicago real estate portfolio while working a full-time job?
A: Yes, and Nate Fernandez proves it’s possible. Many people search “how to invest in real estate while working full time,” and the answer lies in automation, time blocking, and strong vendor relationships. Nate built his Chicago portfolio while keeping a 9-to-5, showing that you don't need to quit your W2 job to become a successful property owner.
Q: What’s the Proviso Corridor and why is it a good place to invest in Chicago real estate?
A: The Proviso Corridor includes Bellwood, Broadview, Hillside, and Maywood. People searching “best Chicago suburbs for cash flow” will find this area attractive due to its lower entry prices, solid rent-to-price ratios, and demand from stable working-class tenants.
Q: What financing options are available for first-time landlords in Chicago?
A: Nate used HELOCs, 401k loans, equity partners, and community banks. If you’re Googling “how to buy rental property with no money,” learn from Nate’s creative strategies to structure deals using other people’s capital while minimizing your risk.
Q: Do I need to hire a Chicago property manager if I work full-time?
A: Not necessarily. Nate self-manages using automation tools like Anago for rent collection and Stessa for accounting. These are great options for part-time landlords looking for “landlord software for small portfolios.” That works for me, but it all depends on what people's time is worth and their ability to manage stress.
Q: What are the best property management tools for Chicago landlords with fewer than 20 units?
A: Nate recommends Anago for online rent payments and screening, and Stessa for bookkeeping. If you're searching for “free landlord software,” these are great places to start.
Q: What’s a realistic rent for 1-bedroom or 2-bedroom units in Broadview, IL?
A: Nate collects around $1,200 per unit, plus additional income from parking and laundry. Google queries like “average rent in Broadview IL” or “rental income in Bellwood IL” can lead investors to consider these cash-flowing markets.
Q: What are typical costs of buying a 4-unit building in Chicago suburbs?
A: In the Proviso Corridor, four-flats range from $350,000 to $450,000. With 25% down and reserves, you should plan for $100,000+ in capital. Many investors looking up “how much to save to buy multifamily in Chicago” will find this number realistic.
Q: How do you deal with village inspections when buying property in Chicago suburbs?
A: Each village is different. Some require electrical upgrades or cosmetic repairs before closing. If you're Googling “village inspection checklist Illinois,” know that understanding local codes is crucial before placing offers.
Q: What are smart ways to scale from 4 units to 20+ units in Chicago?
A: Nate used a strategy called “trading up.” After proving success with his four-flat, he used equity and partnerships to acquire 12- and 16-unit properties. Searching “how to go from 4 units to 20” will show the importance of leveraging appreciation and relationships.
Q: Is it better to flip or hold rental property in Chicago?
A: For Nate, long-term buy-and-hold is the strategy. He wants 100 doors and early retirement. If you’re wondering “should I flip or rent in Chicago?”, consider that consistent cash flow and tax advantages may outweigh one-time flip profits.
Q: What tax benefits are available to Chicago landlords with a W2?
A: Nate offsets rental income with expenses and depreciation. For those Googling “do landlords get tax breaks while working full time,” the answer is yes—and investing through LLCs, using depreciation, and tracking all repairs helps lower taxable income.
Q: How can I teach my kids about real estate?
A: Nate brings his four-year-old to collect coins and meet tenants. If you’re researching “how to involve kids in real estate investing,” small tasks like this build generational knowledge and financial literacy early.
Q: What’s the biggest mistake first-time Chicago landlords make?
A: Over-improving units and doing their own rehab without a cost-benefit analysis. Googling “first rental property mistakes” often returns this advice—delegate early and calculate your opportunity cost.
Q: Where do I find deals on 6-unit and 12-unit buildings near Chicago?
A: Nate worked with broker John Warren and attended local meetups. If you’re searching “off-market deals Chicago multifamily,” networking and attending investor events is still the top way to find them.
Q: What’s the long-term benefit of investing in Broadview or Bellwood?
A: Rents are rising, tenant quality is strong, and value-add potential is high. These communities are adding new development, and prices haven’t peaked yet. This is a solid answer for anyone asking “is Bellwood IL a good place to invest?
Show Notes
00:37 – Meet Nate Fernandez and his 20+ unit Chicago portfolio
02:15 – Why W2 earners shouldn’t delay investing
05:30 – First four-unit deal while expecting his first child
08:00 – Proviso Corridor investing strategy explained
10:45 – Partnering with family to scale: pros and cons
13:20 – Tools for screening, collecting rent, and bookkeeping
17:00 – Managing time, family, and 20+ units efficiently
20:10 – Trading up four-units to 12- and 16-unit buildings
24:00 – How taxes and inspections vary by Chicago suburb
28:10 – Tenant expectations and property finish levels
31:40 – Why investors should plan for rising Cook County taxes
35:00 – Long-term goals: 100 doors and financial freedom by 40
Guest Info
Guest Name: Nate Fernandez
Guest Website: Optimum Process Partners
Because finding good tenants and property management shouldn’t feel like online dating.
Dear Investor,
If you are an investor in either the city or suburbs of Chicago, I would love to speak with you about how we can help you on your real estate journey. At GC Realty & Development LLC we help hundreds of Chicagoland real estate owners and brokers each year manage their assets with both full service property management and tenant placement services.
We understand that every investor’s goals are unique and we love learning about each client’s individual needs. If there is an opportunity to help you buy back your time by managing your rental property or finding quality tenants, please check us out.
Best Investing,
Mark Ainley
Founder, Partner, Podcast Co-Host, and Investor
(1).jpg)
(4).jpg)
