September 2026 SEPTEMBER 2026 | ISSUE NO. 34
NEWSLETTER
OFFICIAL LOCAL NEWSLETTER OF YOUR LOCAL REAL ESTATE INVESTOR ASSOCIATION
NEWS INSIDE:
September Reset: Tech, Trends and Tools As summer winds down and the back-to-school mindset takes
THE NEXT 12 MONTHS OF WORKFLOWS Page 2
over, September marks the ultimate reset for real estate investors. Whether you’re analyzing your very first deal or managing a portfolio of hundreds, staying ahead in the Greater Milwaukee
CAPITALIZING ON REPAIRS & MAINTENANCE Page 5
market requires adjusting your strategy to match the shifting season. As kids return to the classroom, it's time for us to get back to business, sharpen our tools, and commit to mastering our craft. This month, we’re looking past the quick fixes and diving
SAVE MONEY WITH TOOLS AND SOFTWARE Page 9
into the core tools, local data, and community connections that will define your success through the end of the year and beyond. Note: This newsletter contains a few affiliate links. If you click, and purchase, we may receive a small commission at no extra cost to you.
Why the Next 12 Months Will Divide Investors into Two Groups There is a subtle shift happening right now across the market. It isn’t a change in interest rates, and it isn’t a shift in inventory levels. It’s an operational gap—and it’s widening every single week. On one side are investors who operate the exact same way they did five years ago: manually pulling comps, taking days to respond to motivated sellers, letting cold leads die in spreadsheets, and working 60+ hours a week just to keep their heads above water. On the other side is a growing group of leverage-focused investors. They run smaller teams (or operate completely solo), yet they analyze deals in seconds, nurture thousands of seller leads automatically, and make competitive offers before other buyers have even driven by the property.
AI Isn't Replacing Experience, t's Multiplying It If you’ve been on the fence about artificial intelligence and workflow automation, it’s easy to dismiss it as hype. But AI in real estate isn't about asking a chatbot to write a cute social media post. It’s about speed, consistency, and margin protection. Consider where deals actually originate: The Speed to Lead Advantage: When a distressed seller submits an inquiry, the investor who touches that lead within 5 minutes is 9 times more likely to convert them. Humans get busy, get stuck in traffic, or sleep. Automated workflows respond instantly, pre-qualify the seller, and book the appointment on your calendar. The "Dead Lead" Goldmine: Upwards of 90% of real estate transactions don't happen on the first contact—they happen between the 5th and 12th follow-up over 6 to 18 months. AI-driven CRMs re-engage leads automatically with personalized messaging based on seller intent, pulling hidden equity out of database records you already paid for. Underwriting at Scale: Instead of spending 45 minutes running comps and estimating rehab ranges manually, structured AI prompt frameworks let you parse public records, rent rolls, and repair estimates in under two minutes, giving you a firm baseline MAO (Maximum Allowable Offer) before competitors even open their spreadsheets. The Reality: AI will not take your job or steal your deals. But an investor leveraging AI will routinely beat you to them. Continue to the next page for more
How Your Business Model Shifts with AI Integration Whether you are looking for your first house hack or managing hundreds of doors, automation systematically replaces high-friction admin tasks with repeatable systems:
Core Business Function
Traditional Workflows
AI & Automated Workflows
Lead Generation
Cold calling lists or sending one-off direct mail rounds.
Multi-channel, dynamic drip sequences that adjust based on seller response triggers.
Property Underwriting
Manual spreadsheet entry, toggling between MLS, tax records, and maps.
Automated data extraction that populates repair estimates and cash flow projections instantly.
Lead Nurture
Sticky notes, manual CRM reminders, or forgotten follow-ups.
Algorithmic re-engagement campaigns that reactivate months-old "no" responses on autopilot.
Tenant / Buyer Communications
Answering the same 10 routine questions via phone or email daily.
Conversational AI tools handling basic inquiries, screening, and appointment scheduling 24/7.
The Bottom Line At our upcoming Milwaukee REIA Main Meeting, we are bringing in industry expert Damon Remy (Founder of REI BlackBook) to break down these exact systems step-by-step. He’ll be showing us real, actionable blueprints for building an automated lead machine, running instant underwriting, and turning cold contacts into closed contracts without adding staff or working more hours. When: Tuesday, September 8, 2026 | 6:00 PM – 8:30 PM Where: DoubleTree Milwaukee - Brookfield (18155 W Bluemound Rd) Who Should Attend: Anyone looking to buy back their time and close more deals in today's market.
Upcoming Events
JOIN IN WITH SOME LOCAL EVENTS!
SEPT 8
Main Meeting: Using AI & Automation to Buy Back Your Time
SEPT 16
Investor Breakfast Club
SEPT 24
W.I.N.G.S. Luncheon
OCT 13
Main Meeting: STR Guest Experience Masterclass - Turn Every Stay into a 5-Star Story
Dave Graf | 920-203-6087 | dave@gsifoundations.com
Jodi Graf | 414-395-5478 | jgraf@premierpointrealty.com
Taylor Rens | 414-296-6225 | taylor.rens@zrlaywers.com
John Newland | 414-852-0921 jnewland@terranova-realestate.com
Book of the Month
414-276-7378 | membership@aasew.org
Dan Farsht | 262-208-4708 | info@reiahardmoney.com
Tanya Holland | 414-507-4418 | tholland@prisimtitle.com
Scan to see all of our fabulous vendors!
Capitalizing on Repairs and Maintenance BY: JANE GARVEY VIA REALESTATEINVESTINGTODAY.COM
One of the least recognized opportunities in real estate is the call for maintenance or repairs. Most housing providers dread it. It usually means getting our hands dirty, working with contractors, and spending money. It is among the main reasons people say they don’t want to invest in rentals – “tenants, trash and toilets.” What if repair and maintenance calls could be used to build respect, referrals, lasting loyalty and minimize turnover? They are truly a great opportunity if recognized and handled as such. To take advantage of this opportunity we need to put ourselves in the resident’s shoes. How would you want to be treated if you were renting and had a problem? What would be important to you? Responsiveness – As a resident I want to make one call, one text, one email, or one online portal notice and have it start a transparent process. If the problem is an emergency, I want to have a way to reach someone who will treat it as such. If possible, having a friendly, knowledgeable human who can take the call, triage the problem, and then let the resident know what to expect would be ideal. In today’s world of unreachable humans, this would make your operation a standout success.
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Flexibility – Most of our residents have jobs and other obligations. Flexibility of how and when the service is handled is important. Should the resident need to take off work to wait for the maintenance worker? If they want to, great. If not, can you or your maintenance staff handle it without them being there, or at least work around their schedule? Give them choices. They are already inconvenienced by having some of what they are paying for not working. Make it as easy as possible to get it fixed. Friendly – Make sure that you and your staff are treating your residents with respect. You can be a wonderful owner, but if your maintenance staff is surly, rude, disrespectful, or anything but friendly and professional you will not get the same results. Quality – The repairs need to provide a true solution. Cosmetic coverups, temporary patches, and similar “solutions” will not serve you. If they are needed to provide relief while parts come in, make the resident is aware that is what is going on. Let them know what is needed, and what steps are being taken to make that happen. Care and Concern – If I were the resident, I would want it to be evident that all involved in the process want to make things right. I want to see and hear concern that the repairs are being made. I want them to acknowledge that this is an issue for me that I should not be having to deal with. When it is not a problem I caused, I don’t want people being annoyed with me. If I did cause the problem, I want them to let me know what I need to do differently so that I don’t cause it to recur. Attention to Details – The best maintenance people I have, keep their eyes open for other issues when they are making repairs. By doing so, we can get ahead of issues, show concern for the property, and keep things running smoothly. This saves money in the long run and bolsters the image of a concerned housing provider. You may need to have a discussion with your maintenance team to shift their perspective. Communication – You can do everything perfectly, but without the communication piece it will all fall flat. We are living in a world where communication is easy. A text to let someone know that the parts have been ordered and when they are expected to arrive will let them know progress is being made. Checking in with them about schedules, and other concerns is important. If they are having to reach out to you after the initial call, you are falling short on this piece.
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Follow-up – After the repairs are made, check in with your resident to make sure they do not have further issues, and that everything went smoothly. All of these things in combination will make your service stand out. It is a key to long term success. The right attitude about repairs as an opportunity will make the calls easier to take. Once again, put yourself in the resident’s shoes. What would you do if the housing provider didn’t treat your maintenance requests as a priority? I would: Stop reporting minor issues. If I reported something that needed repairs and no one dealt with them, I would probably live with it while becoming increasingly irritated. When the time came for a renewal, I would look for a new place to live. If it was a major problem, I would make follow-up calls, and document them Start using legal means to make the repair – i.e. repair and deduct statutes Adopt alternate solutions where possible. What would you do if the housing provider went above and beyond in taking care of your calls for repairs, provided maintenance on a regular basis, and even asked if there were things you were aware of that needed work? As a resident I would: Work harder to keep things clean and in good repair Stay longer since I have found a housing provider that cares Ask what other units they have available when I need to move. Refer my friends Reach out about minor problems that could become major Alert my housing provider of potential problems around the property When possible, give great reviews on websites or social media. Every time the phone rings with a resident seeking a repair, the opportunity is there for relationship building. Even though you will have an expense for parts and labor, you will have the long-term benefits that come with happy residents. Residents who stay, referrals of new residents, great reviews, less work needed during turnovers since maintenance issues are dealt with as they happen, and fewer if any complaints about rent increases because residents are getting what they are paying for. In addition, when you do have an issue where something doesn’t go as intended, you are more likely to have an understanding flexible resident to work with. This is truly a win-win for treating others as you would like them to treat you.
Milwaukee REIA Vendor Highlight
SVA is a mid-size independent accounting and advisory firm that works with small businesses throughout the country, with over 50 years serving Southern Wisconsin. We are excited to be working with the Milwaukee REIA. Over the years, we have had the opportunity to work extensively with real estate investors in a variety of niches, including buy-andhold investors, fix-and-flip operators, wholesalers, hard money lenders, and other real estate entrepreneurs. We have extensive knowledge of accelerated depreciation options, cost segregations, and like-kind exchanges. We enjoy working with real estate investors to help navigate their tax and financial aspects of growing their businesses. We are glad to be part of the team here at The Milwaukee REIA. Craig Maternowski 262-923-5215
Market Update FOR MILWAUKEE COUNTY
523 Sold Homes
754 New Listings
22
AVG Days on Market
$378k AVG Sale Price
$325k
100.2%
AVG Listing Price
Sales Price Ratio
$781k
100.2%
FOR WAUKESHA COUNTY
413 Sold Homes
461 New Listings
26
AVG Days on Market
$672k AVG Sale Price
AVG Listing Price
Sales Price Ratio
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