New to RE Investing, Looking to Connect in Milwaukee

Dan HandfordPro Member

Investor · Lexington, SC · Member since 2018 · 779 posts · 501 votes

Merek, a sustainable portfolio is easier to design when you translate the long-term goal into operating milestones. I would define the annual income and reserve level the portfolio must produce before your wife leaves her W-2, then work backward to the property type, number of units, capital required, and management workload. For the first purchase, narrowing to one strategy and a few Milwaukee submarkets will make the learning process more useful than comparing every property type at once. Are you leaning toward a house hack, small multifamily, or a conventional single-family rental for the first deal?

Merek WilliamsPro Member

OP

Rental Property Investor · Milwaukee, WI · Member since 2026 · 2 posts · 1 vote

Hi Dan! That was our thought initially and have the annual income amount be equivalent to her W-2 income to have it act as an income replacement for her while allowing us to scale from there.

For the first purchase, some resources and podcasts I have listened to suggested the house hacking for the first few deals as a way to generate cash flow somewhat quickly. The primary focus we had to start was to begin with small multifamily properties to get accustomed to holding the investment properties long-term and the ongoing management of them. We see the diversified approach being beneficial and get used to all kinds of deals.

Curious to know if you recommend one or another for the first deal.

Arman AhmedPro Member

Real Estate Agent · Columbus Cleveland Dayton, OH · Member since 2024 · 2k+ posts · 974 votes

[email protected]614-418-6081

Quote from @Merek Williams:

Hello, everyone! My name is Merek and I am just beginning my real estate investment journey. I work as a financial advisor based in Milwaukee and have been interested in developing a real estate portfolio personally. A number of clients have rental property and know it can appear overwhelming to start, but want to leverage me resources to get my feet under me before taking the leap.

I'm looking to connect with other real estate investors or professionals in the Milwaukee area to learn more about the industry as well as start building a network. The intention is to start the portfolio on the side and build it to a level my wife can leave her W-2 employment to manage the portfolio full-time. We are open to all types of investment properties and wanting to build a sustainable portfolio with modest growth over the coming years. If there are other professionals that want to connect as well, it would be much appreciated.

Thank you for reading and wish you all the best.

Merek

Hey Merek, welcome to the investing side! Since you’re focused on building a steady portfolio over time, I’d also look beyond Milwaukee and compare a few Midwest markets. The Midwest market has some affordable cash flow opportunities, and you can still invest out of state with the right local team in place. For a first deal, I’d focus on buying something that works conservatively from day one and build from there.

Robin SimonBusiness Member

Lender · Austin, TX · Member since 2022 · 5k+ posts · 4k+ votes

Quote from @Merek Williams:

Hello, everyone! My name is Merek and I am just beginning my real estate investment journey. I work as a financial advisor based in Milwaukee and have been interested in developing a real estate portfolio personally. A number of clients have rental property and know it can appear overwhelming to start, but want to leverage me resources to get my feet under me before taking the leap.

I'm looking to connect with other real estate investors or professionals in the Milwaukee area to learn more about the industry as well as start building a network. The intention is to start the portfolio on the side and build it to a level my wife can leave her W-2 employment to manage the portfolio full-time. We are open to all types of investment properties and wanting to build a sustainable portfolio with modest growth over the coming years. If there are other professionals that want to connect as well, it would be much appreciated.

Thank you for reading and wish you all the best.

Merek

Welcome To BP!

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Igor Ganapolsky

Coral Springs, FL · Member since 2018 · 497 posts · 118 votes

Merek, as a financial advisor you already think in terms of risk-adjusted returns and compounding — that's exactly the lens that makes tax deed auctions powerful for building a portfolio fast enough to replace a W-2 income.

The math problem with starting on retail MLS in Milwaukee is that you're buying at full price and hoping for appreciation + modest cash flow. If your goal is to build enough portfolio to replace your wife's income, you need to accelerate equity creation, not just cash flow.

Tax deed auctions solve this by letting you acquire at 50-70% of assessed value. That instant equity spread becomes the engine for portfolio growth:

- Buy a $150K property for $90K at auction → $60K instant equity
- Refinance after rehab at market value → pull most capital back out
- Use that capital for the next acquisition
- Repeat until the portfolio generates enough cash flow to replace the W-2

On retail purchases, that cycle takes years. With auction acquisitions at deep discounts, you're compressing the timeline because each deal starts with built-in equity instead of hoping for it.

I'm working on Broward County (FL) Tax Deed Auction #113 on October 26. There are 16 properties — condos and single-family — all selling at 50-70% of assessed value. The spreads between opening bid and market value range from $80K to $300K+.

Here's why this matters for your W-2 replacement timeline:
- Deep discount basis = instant equity = faster portfolio scaling
- You can hold for rental income (cash flow replaces W-2 over time)
- Or sell immediately after acquisition and take the spread as capital for the next deal
- As a financial advisor, you already understand the numbers — auction acquisitions are basically buying dollar bills for 60 cents

Milwaukee does have tax sale opportunities too (Wisconsin sells tax certificates, and some properties eventually go to deed). The principle is the same: acquire at a basis where cash flow is the default outcome, not the optimistic projection.

If you want to see the specific property breakdown for the Broward auction, I can share the analysis. Always good to connect with someone who approaches investing with a financial planning mindset rather than just chasing deals.

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Seth McGatheyBusiness Member

Real Estate Agent · Milwaukee WI · Member since 2024 · 321 posts · 255 votes

[email protected]708-297-0996

Welcome, would love to connect. I am both an investor and investor friendly agent in Milwaukee. If you still need an agent, happy to talk and see if we would be a good fit to work together. But even if you don't need an agent right now or already have one, I am also a member and leader of AspiRE which is a local investor meetup here in Milwaukee. Our next meetup in in a week (September 9th). In the meantime feel free to reach out and I can connect you with our meetup and Facebook page. But no need to wait until the meetup, feel free to reach out anytime to talk.

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Ashish AcharyaBusiness Member

CPA, CFP®, PFS · Sarasota, FL · Member since 2017 · 5k+ posts · 3k+ votes

[email protected]941-914-7779

Merek, given your background as a financial advisor, you already have a useful lens for this: I’d think about the first property as building a repeatable investment system, not just getting a deal closed.

Since your goal is modest growth over time, I'd start by narrowing the buy box before looking at everything at once. Decide whether you want small multifamily, single-family rentals, BRRRRs, or another strategy, then get very comfortable underwriting that one type of deal. For a first property, I'd care more about stable cash flow, manageable CapEx, and enough reserves than trying to maximize leverage or force appreciation.

From the tax side, I'd also avoid overcomplicating the entity structure before you own anything. An LLC can be useful for legal and organizational reasons, but it doesn't automatically create tax savings. Once the first property is placed in service, depreciation, passive-loss treatment, and potentially cost segregation become much more relevant.

Since you're hoping to build something that eventually runs alongside your advisory business, I'd establish clean bookkeeping, separate banking, property-level reporting, and documented processes early. That will make hiring a VA or property manager later much easier.

Feel free to DM me, I’d be happy to send over a few resources that might help as you start analyzing your first deals.

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Corina Eufinger

Rental Property Investor · Oconomowoc, WI · Member since 2016 · 996 posts · 432 votes

1mo

Hi Merek! Welcome to the world of investing. We're gald you're joingin us! Milwaukee and its surrounding areas have some solid markets. I think you first need to consider if you want to be close to the property, or the maximum distance you want to be from the property. If you plan on self-managing (assuming B&H) then you want to be probably within 30 minutes. If you feel comfortable fleshing out even a minimalistic team for repairs or such, then you can expand your radius without having to hire a PM.

I defer to Rebecca Knox on her knowledge of Mke because she's a rockstar there, but I can help you with consider markets outside the Mke area throughout Southeast and SouthCentral WI.

Let me know how I can help or any referals you need.

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Rebecca KnoxBusiness Member
Specialist · Milwaukee, WI · Member since 2014 · 1k+ posts · 1k+ votes
4w
I just saw this post Corina--what a nice thing to say especially from someone like yourself, who I admire and respect! Thank you very much.
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Harold Yam

Los Angeles, CA · Member since 2026 · 6 posts · 15 votes

1mo

Hi Merek! Just came across your post and wanted to see how your real estate investment journey has been going so far.

I’m actually based in Los Angeles and interested in investing in Milwaukee myself. I’m also looking to connect with a reliable local real estate agent who knows the market well and can help me on the ground.

Would love to hear about your experience so far and whether you’ve made any good connections in the area!

Tomer Markovich

Property Manager · Milwaukee, WI · Member since 2016 · 17 posts · 5 votes

1w

Welcome Merek! Smart move to build the network first. I'm one of the owners of Happy Management, we manage 100+ properties for investors and Milwaukee is our main market. We also own single family rentals on the northwest side.

Happy to connect and share what we learned, from what to watch for in older Milwaukee houses to self managing vs hiring a PM. And if any of your clients with rentals need a second opinion, feel free to send them my way.