10/23/2026
Most agents see a vacation house on its best day.
Typically, it’s staged, cleaned, flowers on the counter, and filled with cozy lighting.
But I spent thirteen years seeing some of them on their worst day.
When Maddy and I purchased Woodfield Properties in 2013, we took over the vacation rental and property management business her parents started in 1983. That also meant inheriting an in-office team Monday through Friday, and someone on call through every night and weekend since then.
Let me tell you, you’ll learn a lot through managing properties. Especially for folks on vacation in W**e Country!
You learn which roofs actually handle a March downpour. Which driveways nobody can find in the dark. Which charming old systems are charming right up until a guest is standing in them.
This gives me lived-in experience and insight for my second-home buyers and sellers.
👀 Here’s what I look for:
As a buyer, what will this house most likely require from you in three years, during a storm, or even a drought? Who’s taking the emergency calls when you’re on vacation? Is the house properly zoned for how you intend to use it?
As a seller, what potential issues are worth fixing now versus negotiating later? Have you had that old oak tree assessed lately? Will any issues arise for the buyers and neighbors about that new fence you just installed?
A showing tells you how a house presents, but ten years of late-night calls, guest feedback, and maintenance logs tells me to ask — how will this house hold up? That’s the answer second-home and STR owners want to know.
