As the holidays approach, condo owners often ask: how should we thank building staff? At 175 East Delaware Place HOA, the 2025 Holiday Fund highlights challenges in governance, fairness, and compliance. Cash gifts are being distributed outside payroll to both HOA employees and contracted management staff, with management staff receiving an additional fiscal year-end bonus. Our latest Substack newsletter dives into the IRS implications, equity concerns, and lessons for boards, residents, and staff.