All Forum Posts by: Micah White

Hey Andrew! Great to see someone with your background stepping into real estate investing—your experience supporting homeowners and investors definitely gives you a strong foundation to build on. I’m also in the Chicago area and working through my own investing journey. The learning curve can be steep, but having a community makes all the difference.

If you ever want to chat about getting started, deal analysis, or local market insights, feel free to reach out. Looking forward to seeing your progress and swapping ideas!

Hey! I’m based in Chicago and always down to connect with fellow investors in the area. Whether you want to swap deal ideas, talk strategy, or just share what’s working locally, feel free to reach out anytime. Building a strong local network has been a game changer for me, and I’m happy to share insights or learn from others.

Hey! You’re definitely thinking through some important details here, which is great. The reserve requirements on conventional loans can be a surprise for many first-time multifamily buyers, especially with today’s higher interest rates and prices.

If you feel the conventional loan reserves are too steep right now, FHA can still be a solid option, especially since it only requires 3.5% down and has more flexible qualification standards. Just keep in mind the FHA mortgage insurance premiums, which add to your monthly costs.

Other options you might consider:

• VA loans, if you qualify, offer zero down and often don’t require reserves.

• Portfolio lenders or local credit unions sometimes have more flexible requirements for multifamily properties.

• Community lending programs or down payment assistance programs in Illinois might be available depending on the neighborhood.

• Some investors even combine FHA loans with gift funds or partnerships to cover reserves or closing costs.

In any case, focusing on building a strong overall financial profile and a clear budget for reserves and ongoing expenses will put you in a better position to move quickly when the right deal appears.

If you want to talk through loan options, deal underwriting, or timing your first purchase, I’ve worked through these scenarios with other house hackers in Chicago and would be happy to share what I’ve learned.

Hey! It’s awesome you’re bringing your arts and interior design skills into real estate—that’s a huge advantage when it comes to staging and creating appealing spaces. You’re right that Chicago’s short-term rental market is pretty tricky due to regulations and competition, so being open to other markets is smart.

When it comes to finding the right areas, whether for long-term rentals or STRs, the key is to look for places with strong rental demand, steady appreciation, and local regulations that support your strategy. Many investors I know explore markets in the Southeast, Texas, and smaller metros where STRs are booming and regulations are more favorable.

If you want, I’d be happy to share some of the markets I’ve seen perform well, plus tips on how to research neighborhood fundamentals and vet properties beyond just aesthetics. Also, combining your design eye with solid market knowledge will make your investment really stand out.

Feel free to reach out anytime to swap ideas or ask questions!

Hey! Great question—finding solid flip opportunities around Chicago under $300k can definitely be done, but it takes knowing which neighborhoods have strong rehab and resale potential.

Some areas I’ve seen perform well for flips within about an hour of the city include parts of:

• Cicero

• Berwyn

• Oak Park (some pockets)

• Hammond, IN (just over the border, but worth a look)

• Certain parts of Gary, IN (for the bold investor)

• Some South Side neighborhoods like Auburn Gresham or Roseland (with careful vetting)

When looking at flips, focus on properties with good bones that need mostly cosmetic or targeted structural work rather than full gut rehabs. Also, pay close attention to local market comps and how quickly similar renovated homes are selling.

If you’re digging into specific areas or deals and want to run numbers or chat through rehab scope and resale strategy, feel free to reach out. Flips can be a fantastic way to build experience and cash flow when done thoughtfully.

What neighborhoods are you considering so far?

Hey, first off—thank you for your service and welcome back to the Chicagoland area! It’s awesome that you’re diving into real estate and looking to connect with others who can share experience and guidance.

I’m also involved in real estate investing around Chicago and working with folks new to the space. If you want to connect over coffee or just swap notes virtually, feel free to reach out anytime. I’ve found that building a network early really helps smooth out the learning curve and opens doors.

Looking forward to seeing your journey take off—let me know if I can help with anything!

Hey, first off—big respect for your discipline and clear thinking at just 22! Living at home and saving aggressively puts you in a fantastic position to get your real estate journey started on solid ground.

Since you’re aiming for single-family rentals in Chicagoland and planning to keep things manageable by doing some maintenance yourself, you’re already thinking like a savvy investor. A couple quick thoughts as you start:

• Focus on neighborhoods where rents comfortably cover expenses (including mortgage, taxes, insurance, and a buffer for repairs). Look for areas with steady demand and good tenant turnover to reduce vacancy risk.

• Learn as much as you can about financing options early on—there are programs for first-time buyers with low down payments, and sometimes down payment assistance grants for certain areas.

• Building relationships with local real estate agents who know investment properties can save you a lot of time and help spot good deals.

• Don’t underestimate due diligence—get thorough inspections and understand local landlord-tenant laws so you’re prepared.

Since you’re just starting out, having a clear, step-by-step plan to learn and act on each part of the process can really pay off. I’ve helped a few people in similar spots map out their first deals and stay focused, so if you ever want to chat through any of this or get pointers on resources, feel free to reach out.

Wishing you the best as you build momentum—you’re on the right track!

Hey—love the intentionality behind your plan and the clarity of your vision. Co-living as a model is still underutilized in Chicagoland, especially in the near north and west suburbs, but the demand for affordable, flexible housing definitely exists—particularly near job centers, transit lines, and medical or university anchors.

You're absolutely right that finding a setup with two separate structures (SFH + coach house/ADU or legal nonconforming layout) is tough—but not impossible. I've helped a few people explore similar strategies here and would be happy to share what I've seen work in places like Berwyn, Cicero, Oak Park, and certain pockets of Evanston and Forest Park. Zoning and occupancy regs vary a lot by suburb, so navigating local nuance becomes key—especially if you’re trying to avoid running into issues with shared housing regulations.

Really excited for you and your family—it sounds like this next chapter could be both financially powerful and values-aligned. If you ever want to connect offline or compare notes, I’d be glad to chat. Always happy to help fellow FI-minded folks map out creative living and investing strategies!

Looking forward to seeing your journey unfold.

Hey Danielle—love this share. Your reflection on “resurrecting the small seed” really resonated. It’s wild how life brings us full circle sometimes, and it sounds like you’re entering this next chapter with the exact mix of clarity and curiosity that commercial real estate needs more of.

Retail in Chicago is a powerful niche, especially with the right eyes on value-add opportunities and community-driven tenants. And honestly, the skills you listed—especially relationship building and communication—are huge differentiators in this space. Deal-making isn’t just numbers; it’s people, timing, and alignment.

I've connected with a few others recently who are also pivoting into CRE, and the ones who thrive are usually the ones who go deep on the process—learning how to source off-market deals, structure win-win terms, and build a strong team around them. If you ever want to swap notes or talk through strategy, I’d be more than happy to connect. There’s a lot of untapped potential in Chicago’s retail scene, and it’s always great to build with others who are playing the long game.

Wishing you a ton of momentum ahead!

Hey! Love that you're putting yourself out there and looking to take action—that’s honestly the most important first step. I totally get where you’re coming from. When you’re just starting out, it can feel like there are a million little costs that add up before you even get the keys. But the good news is there are creative ways to get in the game, even with limited upfront capital.

I work with new investors here in Illinois (I’m based in Chicago) and help them map out beginner-friendly financing strategies like:

• Partnering up (bringing in someone with capital while you bring hustle and time)

• Using seller credits and lender-paid closing options

• House hacking with low down payment loans (FHA, conventional 3–5%, etc.)

• Tapping grants or down payment assistance programs

• Structuring deals that include rehab costs or defer early expenses

If you're willing to learn and hustle, there's always a path forward—and I’d be happy to chat, answer your questions, or walk you through what that first deal could realistically look like. I also offer coaching and deal support tailored for beginners, so feel free to DM or reach out if you want to dive deeper!

You’ve got the mindset—it’s just about building the right plan and network now.