How Sleeping Dog Properties Has Kept Its Skilled Trades Network Intact Across Three Decades of Boston Construction

The plasterer who works on Sleeping Dog Properties’ Beacon Hill projects has been doing ornamental plaster restoration longer than most of his industry peers have been in the business. He knows the difference between how lime putty was mixed in 1890 and what passes for a repair today. He knows which cracks signal structural movement and which are cosmetic. He knows how to rebuild a medallion detail from a surviving fragment without making it look like a facsimile.

Chris Rapczynski, who founded Sleeping Dog Properties in Boston in 1993, has maintained relationships with craftspeople like him for years. That continuity isn’t a given in construction right now. It’s an achievement.

The construction industry needed 439,000 additional workers in 2025 beyond normal attrition and replacement. The projected figure for 2026 rises toward 500,000. About one in five construction workers is over 55. The industry’s skilled trades have a 73 percent annual separation rate — meaning nearly three out of four skilled workers leave their employers each year. Average tenure across the industry is 3.9 years. Replacing a specialized craftsperson can cost up to 213 percent of their annual salary when you account for recruiting, onboarding, and the months before a new hire reaches the productivity level of the person they replaced.

For a firm doing precision luxury work in Boston’s historic districts, those numbers aren’t abstractions. They’re the conditions under which a single departure — a master carpenter, a historic window restoration specialist, an ornamental metalworker — can materially change what projects the firm can take on.

What staying actually costs

Rapczynski doesn’t soften the economics of retention. “We are constantly entrenched with head hunters trying to recruit or steal my people, and so I’m always having to defend against that, which means I have to pay people more than the market,” he has explained. “I think where we make it up is we make it up in durability.”

That’s not a complaint. It’s a statement of priorities. The craft skills that define Sleeping Dog Properties’ project capability — plaster restoration, period-accurate masonry, historic window rehabilitation — took years to develop in the people who have them. They don’t recruit from a general labor pool. The specialty subcontractors who handle finish carpentry to 19th-century profiles, who can match original window glass specifications in a Back Bay renovation, are known quantities who’ve been on Sleeping Dog jobs before. They know the firm’s standards. They know how projects are managed. The relationship itself is part of the quality control system.

At the same time, skilled trades wages rose 3.9 percent in 2025 and are projected to climb another 3.6 percent in 2026 even as the labor market remains short-staffed. The Boston-area construction labor shortage isn’t improving fast enough to bring wages down. For a firm committed to staying above market — as a deliberate retention strategy — that’s an ongoing commitment, not a one-time fix.

The pipeline behind the network

Rapczynski’s approach extends beyond his immediate roster of subcontractors. Sleeping Dog Properties partners with Building Pathways, a non-profit that provides 200-plus hours of hands-on construction training. The partnership is partly civic, partly practical: the construction industry won’t sustain its craft base through compensation alone. Someone has to build the pipeline of people who know how to do things the right way.

YouthBuild Boston, another program the firm supports, offers an intensive 15-week training program with OSHA credentials. These aren’t luxury-specific training programs. They’re entry points into a trades culture that, at the high end, eventually produces the kind of craftsperson who can walk into a Beacon Hill restoration and know what they’re looking at.

“I think we have great humans here,” Rapczynski said of his team. “The human stock of our company is held in the highest regard.”

That phrase — human stock — is worth pausing on. Most construction businesses view workforce management as a cost-optimization problem. Rapczynski describes it as a matter of who the people are. The distinction produces different behavior. A firm that views skilled labor as a cost to minimize will substitute and cut when the market gets tight. A firm that views it as the central asset will pay, develop, and retain even when that’s harder than it sounds.

What continuity actually delivers

Teams with long institutional tenure outperform the industry standard not primarily because of individual skill, but because of shared standards. A plasterer and a project manager who have worked together across a dozen Sleeping Dog jobs don’t need to renegotiate expectations on each new project. They know where the tolerance thresholds are. They know when to flag a problem early. They know how decisions get made.

That shared knowledge is genuinely fragile. It doesn’t survive 73 percent annual turnover. It doesn’t transfer through a job posting or an onboarding session. It accumulates over the length of a working relationship, and it gets tested — and deepened — through the projects that don’t go smoothly.

Three decades in, the relationships Rapczynski has maintained define what Sleeping Dog Properties can do as much as any individual’s credentials. The client who hires the firm for a Back Bay brownstone isn’t just paying for Rapczynski’s judgment. They’re paying for the network that judgment built — and that the firm, year after year, has done the work to keep together.