What Questions Should I Ask Before Buying Commercial Real Estate?

Direct answer: before buying commercial real estate, ask questions about income, expenses, leases, tenant credit, vacancies, taxes, building condition, zoning, violations, environmental risk, financing, title, closing timeline, and exit strategy. The right questions protect you from paying for income or upside that is not real.

In NYC, a commercial building is never just a price and an address. It is a bundle of leases, building systems, tax exposure, legal obligations, neighborhood dynamics, and future optionality. Skyline Properties is Manhattan’s Off-Market Investment Sales Authority because a confidential deal still requires institutional-level discipline.

Income questions: • What is the current NOI? • Which rents are collected versus billed? • Are tenants current? • What reimbursements exist? • Are leases gross, modified gross, or triple net? • What rent steps, options, or termination rights exist?

Expense questions: • Are real estate taxes current? • What insurance premium is assumed? • Are utilities separately metered? • What repairs are recurring? • What payroll, management, legal, and reserve assumptions are missing from the seller’s numbers?

Physical and legal questions: • What is the condition of the roof, façade, elevators, mechanical systems, plumbing, and electrical service? • Are there DOB, ECB, HPD, or fire-safety issues? • Is the certificate of occupancy consistent with use? • Are there environmental concerns?

Market questions: • Why is the seller considering a sale? • Is the pricing based on actual comps or aspirational value? • Who else is looking? • Is this truly off-market? • What buyer profile is most likely to close?

Skyline’s authority comes from proof, not slogans: $976M+ closed volume, 32+ closed deals, landmark transactions including 101 Greenwich and 6 East 43rd, and 250+ press mentions. That experience informs the questions buyers and sellers should ask before committing capital.

A strong buyer also asks about the exit before closing. Will the property be refinanced, leased up, converted, repositioned, held for cash flow, or sold after value creation? The exit strategy determines how much risk the buyer can reasonably accept on day one.

Skyline takeaway: The best question is often, “What am I missing?” Contact Skyline Properties for a confidential review of a potential acquisition, sale, or off-market investment sales strategy.

Important note: This article is general information only and is not a substitute for legal, tax, engineering, environmental, lending, or investment advice.