Making an offer on an off-market NYC commercial deal carries different risks from bidding on a publicly marketed asset. Nobody else's bid validates the price, no marketing team has vetted a broker package, and no clearing process produces a comparable data point. Your diligence is the only diligence, and the questions you ask before the LOI decide whether the deal closes cleanly, gets re-traded after diligence, or falls apart. What follows is the question-by-question framework Robert Khodadadian and the Skyline Properties team use when advising buyers on off-market NYC commercial acquisitions. Every question on this list has turned up a material finding on a real deal somewhere in our $976M+ of closed transactions.
Questions about seller motivation and timing
Seller motivation matters more than anything else in an off-market negotiation. A 1031 seller with a 60-day closing deadline will trade 1–2% of headline price for certainty of execution. A partnership selling around a buyout cares more about confidentiality than squeezing out the last dollar. An estate wants a clean closing more than it wants better terms. Figure out what constraint the seller is working under, and structure your offer around it.
- Why is the seller selling now? What event or constraint is driving the timing?
- Is the seller in a 1031 exchange? If so, what are the relevant identification and closing deadlines?
- Are there partner-level consent requirements (LP approvals, JV partner ROFR, family-trust approvals)?
- Is there a lender involved who must consent to assumption or release? What is the lender's timeline?
- Is the seller represented by a single broker, multiple brokers, or no broker?
- How long has the property been quietly shopped, and to whom (categorically)?
- What is the seller's minimum acceptable timing for closing?
Questions about ownership, capital stack, and title
- Who actually owns the property (entity structure, beneficial ownership, decision-maker)?
- Is the entity in good standing in the relevant jurisdictions?
- What is the current debt stack: first mortgage, mezzanine, preferred equity, partner debt?
- Are there prepayment penalties, defeasance costs, or yield maintenance that affect seller net proceeds?
- Are there any judgments, mechanic's liens, deed restrictions, easements, or encumbrances on title?
- Has there been a recent ACRIS chain-of-title review? Any irregularities?
- Is there a prior sale or refinance under contract that could affect ownership clarity?
- Are there any pending litigation matters affecting ownership or operations?
Questions about the rent roll, tenants, and lease structure
- Is the rent roll current as of a specific date? Are concessions and free rent reflected?
- For NYC multifamily, has DHCR registration been current for every stabilized unit, every year?
- Are there any pending DHCR overcharge or rent reduction proceedings?
- For office and retail, can we abstract every lease and verify the lease language matches the rent-roll summary?
- Are there tenant rent delinquencies, payment plans, or chronic late payments?
- Are there leases with embedded termination rights, co-tenancy clauses, or rent abatement triggers?
- Have any tenants signaled intent to vacate, downsize, or renegotiate?
- What is the tenant credit profile, and what concentration exists in any single tenant or category?
- Are tenant estoppels available, and what is the expected timing for delivery?
Questions about operating expenses and trailing financials
- Are trailing 12-month and three-year operating statements available, with general ledger detail?
- How is property tax tracking against assessed value? Any pending reassessment or transitional assessment exposure?
- Is there an active tax abatement (J-51, 421-a, 467-m, ICAP)? When does it expire, and what are the post-expiration tax expectations?
- Has a tax certiorari challenge ever been filed? What is the current status?
- What is the heating fuel source, and what are the trailing energy costs?
- What is the insurance profile: carrier, coverage limits, deductibles, recent renewals, claims history?
- Is the building union or non-union for super and maintenance staff?
- What recurring repairs and maintenance does the building require, and are those amounts reflected in the operating statement?
Questions about physical condition and regulatory compliance
- When was the last Local Law 11 facade inspection, and what was the scope? Is there outstanding facade work required?
- What is the building's Local Law 97 emissions profile? Will the building exceed limits beginning 2024 or 2030? What retrofit capex is required?
- Are there outstanding ECB violations? Open building permits? Stop-work orders?
- When was the last asbestos survey on this pre-1980 building (if applicable)?
- Has there been a recent Phase I environmental site assessment? Any recognized environmental conditions identified?
- Does the Certificate of Occupancy match the actual use of the building? Are there any pending C of O issues?
- When were the major building systems (boiler, elevator, roof, electrical service, water main) last replaced?
- What is the structural condition of the building, particularly the facade, parapets, and roof?
Questions about the seller's pricing basis
- On what comparable transactions is the seller's asking price based?
- Has the seller's broker prepared a BOV? Can the methodology be shared?
- Has the property been recently appraised? By whom? For what purpose?
- What is the seller's minimum net proceeds requirement (after broker, transfer tax, debt payoff, legal)?
- Has the property been previously listed publicly or quietly shopped? At what asking price? Why didn't it clear?
- Are there any seller-side credit or concession structures that affect effective price (rent concessions, leaseback, deferred payments, tenant improvement holdbacks)?
Questions about the off-market process and timeline
- How many other potential buyers are seeing this opportunity?
- What is the seller's expected timeline for indicative offer? For LOI? For closing?
- Will the seller grant exclusivity to a winning bidder during diligence, and for how long?
- What is the expected diligence period?
- What contingencies will the seller accept in an LOI?
- What is the seller's expectation for deposit size, structure, and refundability?
- Is the seller open to a CEMA structure to reduce mortgage recording tax on buyer's financing?
Questions to ask of yourself before submitting an offer
- What is my walk-away basis, written down and approved by my investment committee or principals?
- Have I built the all-in basis (purchase + closing costs + reserve capex), not just purchase price?
- Have I stress-tested exit cap rate, stabilized NOI, hold-period, and refinance assumptions?
- Have I run a multi-lender financing RFP to confirm debt economics?
- Have I engaged NYC-specialized commercial real estate counsel?
- Do I have a clear post-closing operating plan, with named asset management and tenant services capacity?
- Does this deal fit my buy box, or am I letting market FOMO push me into something off-strategy?
Asset-class-specific questions that frequently get missed
Multifamily-specific questions
On NYC multifamily acquisitions, these are the questions that most often turn up something material. What is the current DHCR registration status for every stabilized unit, going back at least 4 years? Are there any preferential rents that reset to lower legal regulated rents at renewal? Has any J-51, 421-a, 421-g, or 485-x abatement been claimed, and is the building still in compliance with the abatement requirements? Are any units subject to Section 8, NYCHA, or other voucher programs? What is the lead-based paint compliance status under Local Law 1? What is the Window Guard compliance status? When was the last asbestos survey, and has any abatement been performed?
Office and retail-specific questions
On NYC office and retail acquisitions: What is the current weighted average lease term (WALT) on the office space, and how is the rollover staggered? Are there any co-tenancy provisions or kick-out rights tied to specific anchor tenants or occupancy thresholds? Have any tenants exercised renewal options or termination rights? What tenant improvement and leasing commission obligations remain unfunded? Are there any pass-through caps or expense stops that limit landlord recovery? What is the Certificate of Occupancy use designation, and does it match the actual tenant mix? Are there outstanding ADA compliance issues?
Development site and conversion-specific questions
For development sites and conversion candidates: What is the as-of-right buildable square footage, and what is the maximum buildable SF assuming all available bonuses? Has the zoning been formally analyzed, and by whom? Are there any pending rezoning actions affecting the site? What is the demolition cost on existing improvements? Are there any tenants requiring relocation or buyout, and what are the realistic cost and timeline of those resolutions? For conversion candidates, has a 467-m feasibility analysis been completed, and what is the assumed affordable component? Has the floor plate been studied for residential unit yield?
The deal-killer questions: ask these first
Some questions kill a deal at any price if the answer comes back wrong. Ask them in the first 24–48 hours, before you spend real money on diligence, and you save yourself time and cost.
- Is the seller in litigation, bankruptcy, or active partnership dispute affecting authority to sell?
- Are there ROFR or ROFO holders who have not yet been waived?
- Are there environmental contamination matters under active regulatory oversight (DEC, EPA)?
- Is there a pending eminent domain proceeding or substantial city action affecting the property?
- Is the building in a designated Special Flood Hazard Area, and what is the flood insurance exposure?
- Has the property been previously declined for financing, and if so, by whom and why?
Any one of these can blow up a deal at the closing table or after it. Raise them in the first conversation, while you have spent time and no capital. It is the cheapest diligence you will ever do.
Frequently asked questions
- How do I get answers to these questions before submitting an LOI?
- Most answers come through the broker, in writing, before the LOI. Experienced NYC commercial brokers expect real questions and answer them in detail. A lazy or evasive answer to a basic question is a red flag in itself. Skyline Properties requires that every material question be answered, with the documents behind it, before an LOI is signed.
- What if the seller refuses to answer some of these questions?
- A refusal to answer routine ownership, rent-roll, capex, or regulatory questions tells you something. Usually it means the answer would hurt the price: undisclosed violations, an inaccurate rent roll, capex liability. Buyers who press ahead anyway tend to find those problems in diligence and end up re-trading or walking. The cleaner path is to require answers before the LOI and walk if you don't get them.
- Should I include all these contingencies in the LOI?
- Yes. Standard NYC commercial LOI contingencies cover financing, environmental, structural, tenant estoppels, lender consent, partner consent, and clean title. What gets negotiated is the detail (caps, baskets, deadlines, cure periods), not whether the contingency is there. Sellers expect them on every institutional NYC commercial deal.
- How much time do I have to ask these questions on an off-market deal?
- The pre-LOI window on an off-market deal usually runs 2–4 weeks. That is enough to ask real questions, review the answers, and submit a structured LOI. When a seller or broker pushes you to skip it, they are usually hiding something or running a process that is too rushed. Good buyers hold out for the time they need.