The $300,000 Mistake: Why Feasibility and Permitting Comes First

A prospective client came to us recently after spending over $300,000 on what they thought was the beginning of a dream build. They purchased land for $200,000, secured Board of Health approvals for well and septic, and spent another $100,000 on architectural design, engineering, and legal fees. They had a full team. They thought they’d done everything right.

Then the town denied their building permit.

Let’s be clear: the land is buildable. It has health department approvals. It is not landlocked or fundamentally unusable. But what can legally be built there is so misaligned with the client’s intended use—both in form and scale—that there is no version of the project that makes financial, functional, or design sense.

There’s no positive ROI to be found—not in any configuration, not in any workaround.

What Everyone Missed

The problem wasn’t a single line in the code. It was a web of constraints that no one fully mapped:

• Archaic zoning laws that haven’t been meaningfully updated in decades
• Private easements and driveway maintenance agreements that create access and control issues
• A municipal culture steeped in NIMBYism and protectionism, where even compliant projects face obstruction
• A planning board that operates more like a gatekeeping committee than a regulatory body.  

This wasn’t just a zoning issue. It was a political, cultural, and logistical reality that no one on the client’s team had fully accounted for. 

By the time they came to us, the damage was done. Their design, budget, and construction assumptions were dead on arrival. And we couldn’t help—because no legitimate path forward existed under their original goals.

We don’t take on false hope. We don’t do projects just to “try.” If we can’t see a way to win—on paper and in practice—we say no. That’s what integrity looks like.

In this case, saying yes would have been dishonest. They needed to hear the truth, not pay someone else to drag out the inevitable. 

How This Could Have Been Prevented

The tragedy isn’t just the loss of $300,000—it’s how avoidable it all was.

This project should have started with a deep feasibility investigation, including:

• Zoning code breakdowns cross-referenced with site-specific conditions
• Title review not just for ownership, but for easements, covenants, and shared-use agreements
• Early conversations with the building department to test interpretations
• Engagement with local land use consultants and professionals who understand the real dynamics
• Review of planning board minutes to detect patterns in approvals, denials, and resistance points

That’s not overkill—it’s basic risk management. It’s how you find out if your dream aligns with the realities on the ground before you invest in plans, renderings, and engineering.

Most buyers think if land is for sale and has BOH approval, it’s a green light. It’s not. The real questions are:

What does the town want here? What will they allow? What’s the actual political and procedural climate?

Ignoring that is how people end up spending six figures and walking away with nothing.