Submitting an offer on an off-market NYC commercial real estate deal carries different risks than bidding on a publicly marketed asset. There is no third-party validation through competitive bidding, no public broker package vetted by a marketing team, no comparable-deal data point that emerges from a clearing process. The buyer's diligence is the only diligence — and the questions asked before LOI determine whether the deal closes cleanly, re-trades after diligence, or collapses entirely. This guide 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 below has surfaced material findings on real deals across $976M+ of closed transactions.
Questions about seller motivation and timing
Seller motivation is the single most consequential variable in off-market negotiation. A 1031 seller with a 60-day closing deadline values execution certainty more than 1–2% of headline price. A partnership selling around a buyout cares about confidentiality more than maximal price. An estate sale cares about clean closing more than terms. Understanding the constraint that drives the seller determines how to structure your offer.
- 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 major building systems last replaced — boiler, elevator, roof, electrical service, water main?
- 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
For NYC multifamily acquisitions, the questions that frequently surface material findings include: 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
For NYC office and retail acquisitions: What is the current weighted average lease term (WALT) for office; what is the staggered rollover schedule? 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
Each of these can collapse a deal at the closing table or post-closing. Surfacing them in the first conversation, when the buyer has invested only time and not capital, is a high-value discipline.
- 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?
Frequently asked questions
- How do I get answers to these questions before submitting an LOI?
- Most answers come through the broker, in writing, before LOI. Experienced NYC commercial real estate brokers expect substantive questions and respond with detailed answers. Lazy or evasive responses on basic questions are themselves a red flag — Skyline Properties insists that every meaningful question is answered with appropriate documentation before LOI execution.
- What if the seller refuses to answer some of these questions?
- Refusal to answer routine ownership, rent-roll, capex, or regulatory questions is itself information. The most common reason is that the answer would damage pricing — undisclosed violations, rent-roll inaccuracies, capex liability. Buyers who proceed despite refusal routinely surface these issues during diligence and end up re-trading or walking. The cleaner path is to insist on pre-LOI answers and walk if they are not forthcoming.
- Should I include all these contingencies in the LOI?
- Yes. Standard NYC commercial LOI contingencies include financing, environmental, structural, tenant estoppels, lender consent, partner consent, and clean title. The negotiation is on the specifics — caps, baskets, deadlines, cure periods — not on whether the contingency exists. Sellers expect these contingencies on every institutional NYC commercial transaction.
- How much time do I have to ask these questions on an off-market deal?
- Pre-LOI period is typically 2–4 weeks on an off-market deal — enough time to ask substantive questions, review answers, and submit a structured LOI. Sellers and brokers who pressure buyers to skip this period are typically hiding something or running an inappropriately compressed process. Disciplined buyers insist on adequate pre-LOI questioning time.