All Forum Posts by: Pat Parrillo

The first, and most critical, step is to determine the property's After Repair Value (ARV). Knowing the ARV clarifies whether investing further is worthwhile or if it's best to exit now.

If the ARV is high enough, you have several viable options:

- Complete critical repairs (roof, foundation), incrementally update units, gradually raise rents, and potentially refinance later to improve cash flow.

- Alternatively, complete the repairs and sell at top market value, maximizing your return despite the short-term headaches.

However, if the ARV is too low and won't justify the $50K+ in repairs plus remote-management stress, You might be better offer selling now, even at a loss. Sometimes it's better to take the L sooner than later, learn from it, and move on. If the numbers don't work now, and they don't work in the future, better to get rid of it now.

Aaron, your strategy of leveraging equity through refinancing to pull out tax-free cash while maintaining cash flow makes a lot of sense, especially with the stability of W-2 income. Many investors use this "infinite leverage" approach to maximize liquidity and tax efficiency. However, interest rate risk is a key factor—if rates rise or lending conditions tighten, refinancing may not be as favorable. Having a backup plan, such as a HELOC or alternative financing options, could provide added flexibility.

With loans spread across 19 single-family homes, consolidating into a portfolio loan might simplify management and offer greater long-term stability. Since your goal is to subsidize retirement, it’s worth considering how much leverage you want to carry as you transition out of your W-2 jobs. Would you eventually scale down to fewer properties with higher cash flow, or continue holding indefinitely? Your plan works as long as cash flow remains strong and refinancing remains accessible—but are you confident that will always be the case?

If you haven’t already, take a look at the 18.6-year real estate cycle and where we currently stand. It could provide valuable insight into timing your refinances strategically across 3, 5, 7, or 10-year terms to hedge against market fluctuations and avoid unnecessary risk.

Investing in Milwaukee for the last 10 years I'm biased to recommend house hacking a duplex as the best way to start if you have limited capital. Milwaukee has the largest duplexes per capita ratio in the US. So let's of properties to choose from. By house hacking It lets you get in the game with minimal money down (3-5%), while also covering your mortgage and gaining real-world landlord experience. If you don’t like it, you can always pivot and sell, convert to a long-term rental, or move into another investment strategy with the equity and knowledge you’ve built.

Starting this way means you’ll go through every key step: finding a deal, securing financing, managing tenants, and understanding property operations, but in the lowest-risk way possible. Plus, owner-occupied loans get the best terms, making it an easy entry point. If I were starting over, I’d go this route again without hesitation.

For Milwaukee, look at Riverwest, Bay View, and West Allis as each have strong rental demand with room for appreciation. The key is finding a property where rents cover the mortgage or, even better, cash flow. Let me know if you want to talk Milwaukee strategy. Also, check out the Rental Property Association of Wisconsin. www.rpawi.org good networking with other investors and maybe even find a deal there. Has been a great resource hope to catch you at a meeting. Keep taking action and at the same time be patient :) 

I gave a presentation on this exact topic at the Rental Property Association of Wisconsin Annual Convention last year, and the key takeaway was that all rental strategies have their merits, but you need to know what you’re signing up for. Some can be passive investments, while others are full-fledged businesses.

Long-Term Rentals (LTRs) are the best starting point for most investors because they offer consistent income, lower management demands, and a truly passive approach. A 12-month lease means stable cash flow, fewer turnovers, and minimal involvement, especially if you use a property manager. Financing is also easier since lenders prefer predictable rental income over the fluctuations of STRs or MTRs.

Short-Term Rentals (STRs) and Mid-Term Rentals (MTRs) can be lucrative but require more hands-on management. STRs, in particular, are closer to running a hospitality business than a passive investment, with constant guest turnover, cleaning coordination, and regulatory risks. MTRs fall somewhere in between but still require furnishing and active tenant acquisition. If your goal is long-term wealth with minimal effort, LTRs are the best place to start, allowing you to scale without making real estate your full-time job.

Congrats on jumping back in @Torrean Edwards! That first deal after a break can feel like a big leap, but it sounds like a great opportunity.

On financing, seller financing, private lenders, or portfolio loans from local banks could be worth exploring if you want alternatives to hard money.

Excited to see how this deal goes for you.

Not a dumb question at all, but getting a $100K loan with no track record is difficult. Traditional lenders won’t approve it, and hard money lenders who offer this type of financing all the time look for experience, assets, or strong equity in the deal.

Partnering with someone who has financing or experience is realistic approach when starting. That could mean working with an investor willing to fund the deal for a share of the profits or starting smaller with a house hack or live-in flip to build credibility, or putting sweat equity into a deal with a partner to learn and build your track record. All of these come back to one important factor, you need to bring value to the table while mitigating risk.

Lenders, Investors, Hard Money, Partners will focus on experience and risk, so bringing value by finding great deals or managing renovations, can help you break in.

Keep refining your approach and connecting with the right people!

Welcome to Milwaukee, Chelsea! House hacking is a smart way to get started, and Milwaukee has some great multi-family opportunities if you buy right. Since you’re in research mode, getting familiar with neighborhood-specific trends will be key, some areas have strong rental demand, while others can be trickier to manage. 

Financing can make a big difference, and local lenders who understand house hacking and multi-family investing can sometimes offer more flexibility than big banks. Even if you plan to self-manage, having a solid property management contact early on is always a good move. Networking will also be huge in your journey. The Milwaukee REIA https://www.milwaukeereia.com/ and the Rental Property Association of Wisconsin https://rpawi.org/ are both great for connecting with experienced investors, lenders, and property managers. I’m a member of both, as well as an agent and investor, and they’ve been great resources.

Hope to meet you at an event soon and always happy to talk shop about the Milwaukee market or multi-family investing. Best of luck on the exciting journey ahead!

Hi @Adam Aero

It's good to have goals in mind. My first question would be why $275K? Is there significance to this exact number?

Knowing your current state comps is a great place to start and a real estate agent can help pull those figures quickly. 

If you’re below $275K, focus on high-impact upgrades like improving curb appeal (landscaping, fresh paint), refreshing the kitchen and bathrooms (new hardware, lighting), or adding energy-efficient features (smart thermostats, LED lighting). Outdoor spaces like a deck or patio can also boost value. I'd recommend starting with the lower hanging fruit than a large basement reno - if your comps are close but don't quite get you to your number.

Finishing the basement (with proper egress) could push you over the top, but confirm with an appraiser first to ensure it counts. Talking to an appraiser early is a smart move—they can guide you on what improvements will add the most value.

Don’t forget to fix any deferred maintenance and highlight unique features like tall ceilings or original hardwood floors.

Let us know how it goes, and feel free to ask more questions—we’re here to help! Good luck.

Great question. Here are some trends that could play out, or further develop in 2025.

Leasing & Tenant Experience 
AI-Powered Leasing: Chatbots and AI tools will streamline leasing processes, from answering tenant inquiries to scheduling tours.
Virtual Tours & Digital Leasing: These will become even more standard, making it easier for tenants to rent remotely.

Technology
Smart Property Management: IoT devices (smart locks, thermostats, etc.) will become more common, improving efficiency and tenant satisfaction.
Property Management Software: Platforms will integrate more AI for predictive maintenance, rent collection, and financial reporting.

Sustainability
Green building practices and energy-efficient upgrades will be a major focus, driven by tenant demand and potential incentives.

AI & Automation
AI will play a bigger role in tenant screening, rent pricing optimization, and even predicting market trends.
Automation will handle repetitive tasks like maintenance requests and lease renewals, freeing up PMs for higher-level activities.

I'm sure there are plenty more shifting trends that I haven't mentioned and that are sure to evolve over the next year. 

Welcome Shea. Congrats on owning a duplex at 20—that's very impressive! For scaling your portfolio, consider house hacking another multi-family property to minimize living expenses while building equity. The BRRRR method (Buy, Rehab, Rent, Refinance, Repeat) could also be a great strategy to recycle your capital.

To find deals, try direct mail campaigns targeting absentee owners or distressed properties, or go driving for dollars in neighborhoods with strong rental potential. Networking with local wholesalers and real estate agents who specialize in investment properties can also lead to off-market opportunities. Online platforms like Zillow, PropStream, and Auction.com are worth exploring, and don’t forget to check out local real estate groups for deals and partnerships.

Since you're in Racine, the Rental Property Association of Wisconsin and Milwaukee REIA are great resources for networking, finding contractors, and learning about funding opportunities. Maybe we'll cross paths at a meeting!

Keep crushing it, and feel free to reach out if you have questions—excited to see where your journey takes you. You've already got a fast start.