| I wrote in May: “In the past 5 years it’s been harder to buy a home than in decades.” Why? Supply and demand.
That cliché about all real estate being local? True. Forget about national headlines. One example is days on market. In Sanibel, FL homes sit on market an average of 261 days. In Wauwatosa, WI, 5.
Sometimes clients come to us having worked with a traditional agent. After a coffee talk meeting I’ll ask, “Are we anything like the other agent you worked with?” When they reply “no” I know we’re doing our job.
I accept you shouldn’t trust us 100% the first time we meet. I wouldn’t. I’d want to trust but verify. What clients most often note and appreciate is our direct and deep approach to looking at housing. We’re not going to tell you what we think you want to hear. We’re going to tell you what you need to know. Your money is involved.
 But sometimes people don’t like the truth because truth can hurt so every 3-4 years, we get fired by a client. As best I can determine, it’s because we won’t sell them a home. We won’t say, “Isn’t this a lovely kitchen?”
Sift through truth vs. marketing/selling. Each is different, with some common elements. Marketing/selling doesn’t involve lying, (absence of truth) but may involve an absence of information. The best way to remove the absence is to dig, dig for information.
If your goal is to own a home don’t be put off by the truth, embrace it and work with it. Truth can change based on local market conditions so we monitor those conditions.
Here’s some truth. When I say can’t, it means in today’s Milwaukee metro market. At this moment. In theory you can, in practice you can’t. Buckle up:
1. You can’t make an Offer subject to the sale of your home.
2. You can’t have a complicated Offer. The cleanest Offer with the best price will win. You may have to waive the appraisal and radon contingencies. You may also have to put a cap on your inspection contingency.
3. No matter the rationale of agents, asking price is probably not value. Generally, you’ll pay more than asking price to get an Offer accepted. We monitor ask vs. sale price for areas because we’re advising you on how to spend your money.
The critical piece? It’s important you know the home’s value, not just asking price. Said another way, if the asking price is $475,000 and you pay $500,000 – but the value is $450,000 – you paid $50,000 more than value, not $25,000. It’s why we prepare a market analysis before an Offer is made.
4. Math. The median sale price of homes in the Milwaukee metro area increased 53% over the past 5 years. The median income increased 20%. (Wisconsin Policy Forum)
5. The days of making an Offer and expecting a counter Offer are gone. Your first Offer must be your best Offer. Visualize your Offer lined up against others.
6. Homes generally come on market on Thursday but may have been listed as “delayed” a week earlier to gin up interest. Sellers review Offers (plural) on Saturday/Sunday and accept one. There are exceptions, but few.
7. You can’t buy a home with 5% down. In theory you may, but in practice you can’t, because 10% is needed to cover a potential appraisal gap.
 8. You won’t get 10 out of 10 things you want in a home. You may get 7-8. You’ll have to decide which 2-3 you can live without.
9. A “cash” Offer, with a mortgage, puts you in a better position to have your Offer accepted. If you are young, check in with mom and dad.
When are the cities Chicago, Milwaukee and New York ever mentioned in the same sentence? Never.
Then this, a report by Bankrate, a financial services firm. Their 2026 study of 100 metro areas found Chicago, New York and Milwaukee as cities where homebuyers have the least amount of leverage. That defines Harder.
As you begin your home search ask 3 questions: Where are you today? Where do you want to go? How do you intend to get there?
What I know from basketball: You’ll always miss 100% of the shots you don’t take. In these hard times the same holds true for real estate.
 Be careful. If you’re buying a home you’re putting money at risk. Get information from sources you trust, then make your housing decisions.
If you are startled by the reality of real estate and have real estate questions, contact me at: homebuyeba@gmail.com
Thanks for reading,
Michael D. Holloway
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