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About Me

A Licensed Vermont Home Inspector Looking After Your Property
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About Me

Three Decades of Knowing Where Houses Hide Trouble

I’m Joby McDonald, a licensed Vermont home inspector, ASHI member, and the owner of Checkpoint Property Care. For more than 30 years I’ve made a living spotting the problems most people walk right past: the faint water ring under a sink, the furnace that keeps short cycling, the gutter that’s been dumping meltwater against the foundation all spring. Property care is the natural next step for that experience. Instead of seeing a house once before it changes hands, I get to look after it season after season.

My path started in South Florida in the early 1990s, where I worked with home inspectors on the marketing side before earning my own credentials in 1992. I studied industrial drafting at Baker College and spent 20 years in the construction industry, which taught me how houses go together and how they come apart. After 9/11 I moved to Vermont to be closer to family, and in 2005 I opened Checkpoint Property Inspections. More than 5,000 inspections later, I started Checkpoint Property Care for owners who need someone they trust keeping an eye on things.

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Straight Talk

If something looks off, I tell you plainly and explain what it means. No alarm bells over small stuff, and no glossing over the things that matter.

Thirty Years of Instinct

Three decades as a home inspector means I notice the subtle signs, like a new odor, a slight sag, or condensation where there shouldn't be any.

One Familiar Face

You won't get a rotating crew. I'm the home inspector who visits, the one who writes your report, and the one who answers when you call.

Why Vermont Owners Want a Home Inspector Watching Their Property

Hiring a home inspector for property care might sound like more than you need until you think about what’s at stake. A seasonal home, an investment property, or a family camp is a big part of your life and your finances. Leaving it unchecked through a Vermont winter is a gamble, and a quick drive-by can miss something like a slow leak or idle sump pump that a trained eye would catch right away. I work out of Irasburg, serve properties throughout the state, and treat every house like it sits on my own land.

If you’re buying or selling a home, my sister company, Checkpoint Property Inspections, handles full pre-purchase and pre-listing home inspections throughout Vermont.

Photo Reports After Every Visit

Each scheduled check produces a PDF report, so you can follow your property's condition from anywhere.

There Day or Night

I'm available 24 hours a day, 7 days a week. Storms, alarms, and frozen pipes don't keep business hours, so I don't either.

Locally Located in the NEK

I'm locally owned, with my base office in Irasburg. When you call, you reach someone who knows the back roads, the weather, and the community.