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Author: Mark Ainely | Partner GC Realty & Development & Co-Host Straight Up Chicago Investor Podcast

Lake County real estate investing offers opportunities that many Chicago investors overlook, especially when it comes to value-add multifamily properties, short-term rentals, and furnished housing.

But scaling a portfolio requires more than finding properties at the right price. You need financing, contractors, property management systems, and a team that can handle the operational challenges of different rental strategies.

In this episode of the Straight Up Chicago Investor Podcast, Tom Shallcross and Mark Ainley welcome back Bill Powers, who first appeared on episode 6, along with his daughter Shannon Powers.

Since that original conversation in 2020, Bill has expanded his real estate business into larger multifamily properties, commercial real estate, short-term and mid-term rentals, and third-party property management.

Bill and Shannon now oversee a portfolio of approximately 350 units, including around 80 furnished rentals. They share how they have scaled in Waukegan, Libertyville, Grayslake, Highwood, and other Lake County communities while learning some expensive lessons from investing in Florida.

The conversation covers value-add investing, raising private capital, short-term rental management, Airbnb arbitrage, property management software, off-market acquisitions, and why understanding operations is just as important as understanding the numbers.

Questions We Answer in This Episode

Q: What is the housing provider tip of the week?

A: Mark recommends considering artificial turf for small yards, rental property common areas, and suitable outdoor spaces. While the initial installation costs more, it can reduce ongoing landscaping expenses, especially at properties with heavy tenant or pet traffic. Structural problems such as deteriorated balconies still need proper repairs before any cosmetic improvements.

Q: Who are Bill and Shannon Powers?

A: Bill and Shannon Powers are Lake County real estate investors and operators involved in Secure Real Estate Management. Bill has spent years building a portfolio of single-family, multifamily, and commercial properties. Shannon joined full-time in January 2026 and oversees asset management and investor relations.

Q: How has Bill's portfolio changed since his first podcast appearance in 2020?

A: Bill expanded beyond single-family rentals and flips into larger value-add opportunities. His acquisitions included a distressed 48-unit building in Waukegan and a roughly 37,000-square-foot commercial property in Grayslake that went from approximately 30% occupancy to nearly full occupancy.

Q: What did Bill learn from investing in Florida?

A: Bill's team built 25 homes in Florida as part of a larger investment plan. Although the properties continue to generate cash flow, property values declined by roughly 20% to 25%, reducing their expected equity. The experience reinforced the importance of maintaining sufficient capital and underwriting investments for changing market conditions.

Q: How do Bill and Shannon raise money for real estate investments?

A: They raise capital deal by deal rather than through a single investment fund. Bill and his wife typically invest significant personal capital alongside outside investors. Shannon manages investor communications, agreements, quarterly distributions, and ongoing reporting.

Q: Why do furnished rentals generate so much revenue for their business?

A: Approximately 80 of their 350 units are furnished rentals, yet Bill says they generate around 40% of portfolio revenue. A Waukegan property that might rent for $2,000 per month as a long-term rental could generate $4,000 to $5,000 furnished, depending on demand and occupancy.

Q: What makes short-term rental management different from traditional property management?

A: Bill describes furnished rental management as a hospitality business. Operators must manage cleaners, linens, supplies, internet, utilities, guest communications, landscaping, maintenance, and frequent turnovers. Their team handles approximately 200 to 250 turnovers per month.

Q: What is Airbnb rental arbitrage, and how does Bill use it?

A: Rental arbitrage allows a tenant to lease a property from the owner and then furnish and operate it as a short-term rental with the owner's permission. Bill receives the agreed long-term rent while the operator manages bookings and guests. However, he limits exposure to individual operators because of potential credit risk, guest misconduct, and municipal compliance issues.

Q: How do Bill and Shannon protect their short-term rental properties?

A: They use minimum stay requirements, noise-monitoring sensors, exterior cameras, guest screening, and communication with neighbors and local officials. They also maintain property rules designed to discourage parties and protect their relationships with surrounding communities.

Q: Where do Bill and Shannon see future investment opportunities in Lake County?

A: Bill remains interested in Grayslake and Libertyville, particularly distressed properties that can be renovated and better managed. Their future plans include larger acquisitions, repurposing underused buildings, and evaluating a proposed 43-unit new construction development.

Show Notes

02:01 Housing provider tip: reducing landscaping expenses with artificial turf at rental properties
03:32 Bill and Shannon Powers return to discuss six years of growth in Lake County real estate
06:20 Acquiring a property management company and scaling into larger value-add multifamily deals
08:49 Investing in Florida, falling property values, and protecting cash flow when equity declines
12:03 Shannon's role in investor relations, raising private capital, and managing quarterly distributions
17:14 How 80 furnished rentals generate approximately 40% of portfolio revenue
20:26 Short-term rental management expenses, cleaning operations, and hospitality challenges
28:21 Finding profitable short-term and mid-term rental properties in Libertyville and Lake County
31:21 Airbnb rental arbitrage, lease protections, and the risks of third-party operators
40:44 Future Lake County investment opportunities, new construction, off-market deals, and financing strategies

Takeaways for Chicago Property Managers and Landlords

Lake County offers opportunities for investors pursuing multifamily, mixed-use, and furnished rental properties.
Value-add investing requires the ability to renovate properties, improve management, and increase income.
Investors should evaluate both cash flow and equity growth instead of relying entirely on appreciation.
Short-term and mid-term rentals can generate substantially more revenue than traditional leases, but they also require more management.
Furnished rentals should be underwritten with cleaning, utilities, furniture replacement, supplies, and management expenses included.
Having a mix of long-term and furnished rentals can create more predictable income while preserving revenue upside.
Proximity to demand drivers such as Naval Station Great Lakes can support furnished rental demand.
Investor relations become increasingly important as the number of outside investors grows.
Rental arbitrage can provide predictable rental income, but landlords must understand concentration risk and local regulations.
Short-term rental operators should maintain positive relationships with neighbors and municipalities.
Relationships with brokers can uncover off-market opportunities before they become widely available.
Strong financing, renovation, and property management teams are essential to successful value-add investments.

Guest Information

Guest Name: Bill and Shannon Powers

Guest Company: RTO Property

Guest Link: https://rtoproperty.com/

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,