Most lists of questions to ask a realtor are written for someone buying a house, anywhere, and run to eight or nine questions about experience and communication. None of that is wrong; none of it is what decides a condo purchase. This list assumes a Pearl District condominium, where the building's finances matter more than the unit's finishes and whether a lender will touch the building matters more than either.
Most of these go to your agent. The last group goes to the association or the building manager directly, because there are answers no agent has. Print the list, or keep it open on a phone. The value is less in any single question than in asking the identical set three times — the gap between a specialist and a generalist is obvious side by side and invisible one at a time.
1. Track record in the Pearl
BothEverything else depends on these. An agent without Pearl District volume will be honest, hardworking and learning on your transaction.
1
How many Pearl District condos have you closed in the last twelve months?
- Why ask it:
- Separates a Pearl specialist from a Portland generalist who takes Pearl clients.
- A good answer:
- A specific number, offered without hedging, plus the buildings.
2
Which buildings have you personally transacted in?
- Why ask it:
- Building-level experience is what transfers; neighborhood experience largely does not.
- A good answer:
- Names buildings, and can say what is distinctive about each.
3
Have you worked in my building before? What did you learn about it?
- Why ask it:
- The single highest-value answer available in this whole list.
- A good answer:
- Specific detail — a board dynamic, a known maintenance item, a quirk in the docs.
4
What share of your business is Pearl District condominiums rather than houses elsewhere in Portland?
- Why ask it:
- A condo is a different product, and the Pearl is a different market from the east side. Volume in houses does not carry over.
- A good answer:
- A majority in condos, and honesty when the answer is no.
5
Can you show me two recent transactions in comparable buildings?
- Why ask it:
- Listing photography and copy quality are visible in seconds, and predict yours.
- A good answer:
- Pulls them up immediately.
6
When did you last advise a client to walk away from a Pearl building, and why?
- Why ask it:
- Tests whether they say inconvenient things. An agent who never has is either inexperienced or agreeable.
- A good answer:
- A concrete story with a reason you can evaluate.
2. Building knowledge
BothThe Pearl is a collection of very different buildings — converted warehouses, mid-2000s mid-rises, recent towers — and the differences are financial, not aesthetic.
7
How many units in this building are on the market right now?
- Why ask it:
- Your direct competition if you are selling; your negotiating leverage if you are buying.
- A good answer:
- A number, and how they compare unit by unit.
8
How many sold here in the last twelve months, and at what price per square foot?
- Why ask it:
- Same-building sales are the only genuinely comparable data point.
- A good answer:
- Pulls the figures from RMLS rather than quoting neighborhood averages.
9
How many listings in this building expired or were withdrawn without selling?
- Why ask it:
- The record of what buyers refused to pay. Rarely volunteered.
- A good answer:
- Knows, or offers to check before the next conversation.
10
Is this a conversion or purpose-built, and what does that change?
- Why ask it:
- Converted warehouse lofts carry different envelope, glazing and systems risk.
- A good answer:
- Explains the practical consequences, not just the history.
11
What is the building's construction era, and are there known envelope or water-intrusion issues?
- Why ask it:
- A real regional concern for Pacific Northwest buildings of certain vintages.
- A good answer:
- Treats it as a normal diligence question, not an insult.
12
How much of the building is commercial floor space?
- Why ask it:
- Ground-floor retail is the Pearl norm, and above certain thresholds it affects conventional financing.
- A good answer:
- Understands why the question is being asked.
13
How is parking held here — deeded, separate tax lot, assigned or leased?
- Why ask it:
- All four arrangements exist in the Pearl, sometimes in neighbouring buildings, and only the first two are an asset a lender will count.
- A good answer:
- Knows for this specific building, and produces the plat or deed rather than assuming.
14
Can this view be built out? What is still undeveloped nearby?
- Why ask it:
- The Pearl is a master-planned redevelopment of the Hoyt Street rail yards and not every parcel is finished. An outlook over open ground is not a permanent one.
- A good answer:
- Knows which neighbouring parcels are entitled or in planning, and says so unprompted.
15
What is directly below this unit — retail, a restaurant kitchen, the loading dock?
- Why ask it:
- Ground-floor commercial is the Pearl norm. Extraction fans, late bar hours and delivery bays are a discount that comparable sales will not reveal.
- A good answer:
- Has been in the unit at more than one time of day.
16
Which street does this face, and what does that do to noise?
- Why ask it:
- Everett and Glisan run one-way toward the freeway. A cross-street unit and a couplet unit in the same building are different products.
- A good answer:
- Suggests opening a window during the showing.
17
What is the rental cap, and how close is the building to it?
- Why ask it:
- Decides whether the unit can ever be let, which matters to investors and to your future exit.
- A good answer:
- Knows the cap and the current count.
3. HOA and financials
BothThe association's finances are your finances. Oregon does not mandate a reserve funding level, which puts this squarely on the buyer.
18
What do you look for when you read board minutes?
- Why ask it:
- The best proxy for whether an agent reads them at all. In this district the recurring items are podium decks, window and glazing systems, and garage membranes.
- A good answer:
- Describes a hunt — repeat repairs, contentious votes, insurance renewals, anything an attorney attended.
19
What is the reserve fund balance and percent funded, and when was the last study?
- Why ask it:
- An underfunded reserve is a special assessment you have not been told about yet.
- A good answer:
- Has the figures, or knows exactly which document to pull them from.
20
Has there been a special assessment in the last five years? Is one pending?
- Why ask it:
- Past assessments predict future ones, and a pending one is negotiable at purchase.
- A good answer:
- A clear answer with amounts and dates.
21
What does the HOA fee actually cover here, and how has it moved over five years?
- Why ask it:
- A fee that has not risen in five years is often a board deferring maintenance.
- A good answer:
- Reads a rising fee as normal and a flat one as a question.
22
Is the association involved in any litigation, including construction defect claims?
- Why ask it:
- Affects financing, insurance and resale at once. Defect litigation over building envelopes is a known pattern in Pacific Northwest condo stock of certain vintages.
- A good answer:
- Knows the status and can explain what it does to a conventional loan.
23
What does the master policy cover, what is the deductible, and who pays it when water travels between units?
- Why ask it:
- In a stacked building one failed supply line becomes several owners' problem, and the deductible can land on you rather than the association.
- A good answer:
- Explains the split, names the deductible, and suggests reading the certificate itself.
24
What is the HOA delinquency rate?
- Why ask it:
- Owners not paying is both a lending threshold and a warning sign.
- A good answer:
- Recognises it as a standard lender question.
4. Questions for the HOA or building manager
BothThese go past your agent. An association or on-site manager has answers no licensee holds, and asking directly costs nothing but an email.
25
How many units are owner-occupied versus rented right now?
- Why ask it:
- Investor concentration is a live threshold for conventional lending, and it moves year to year.
- A good answer:
- A current count, not a percentage from an old marketing sheet.
26
Is the building at its rental cap, and is there a waiting list?
- Why ask it:
- Decides whether you could ever let the unit, which shapes your exit as much as your use.
- A good answer:
- The cap, the current count and the queue length.
27
What capital projects are planned in the next five years, and how are they funded?
- Why ask it:
- The gap between the plan and the reserve balance is the special assessment you have not been told about.
- A good answer:
- A named list with dates, tied to the reserve study.
28
How many owners are more than sixty days delinquent on dues?
- Why ask it:
- A standard lender question, and a direct measure of the association's health.
- A good answer:
- A number, given without defensiveness.
29
What is the master policy deductible, and who pays it in a unit-to-unit water loss?
- Why ask it:
- In a stacked building a burst supply line becomes several owners' problem, and the deductible can land on you.
- A good answer:
- The figure, plus how the association has allocated it in past claims.
30
Are there restrictions on renovations, flooring or window coverings?
- Why ask it:
- Hard-surface flooring rules and uniform window treatments are common in Pearl buildings and rarely mentioned in listings.
- A good answer:
- Points you to the specific rule rather than summarising it.
31
How do move-ins work — elevator reservation, permitted hours, deposit?
- Why ask it:
- A practical constraint on closing day, and a signal of how the building is run.
- A good answer:
- A clear procedure and the deposit amount.
5. Financing and warrantability
BuyersThe question most likely to end a Pearl District purchase in week three of escrow, and the one most often asked too late.
32
Which Pearl District buildings do you know to be difficult to finance, and why?
- Why ask it:
- A real answer names buildings. A vague one means they have not hit the problem yet.
- A good answer:
- Names buildings and gives the specific reason for each.
33
Is this building warrantable for conventional financing?
- Why ask it:
- Determines whether your buyer pool at resale is everyone, or only cash.
- A good answer:
- Knows, or says precisely how and when they will confirm it.
34
Is it FHA or VA approved?
- Why ask it:
- Approval status decides whether a large category of buyers can purchase here at all.
- A good answer:
- Checks rather than guesses, and knows approvals expire.
35
Will the HOA complete a lender questionnaire, how long does it take and what does it cost?
- Why ask it:
- A slow or uncooperative association can blow your financing timeline.
- A good answer:
- Quotes a turnaround from experience.
36
Do you have a lender who regularly finances condos in this building?
- Why ask it:
- A lender familiar with the building is worth more than a marginally better rate.
- A good answer:
- Names one, and is upfront about any referral arrangement.
6. Agency and compensation
BothWho the agent works for, and how they get paid. Both have been reshaped by the practice changes that took effect in August 2024.
37
Who do you represent in this transaction, and what duties does that create?
- Why ask it:
- You are entitled to a plain answer, and Oregon requires the disclosure pamphlet at first contact.
- A good answer:
- Answers directly and hands you the Initial Agency Disclosure Pamphlet.
38
Might you or your firm end up representing both sides?
- Why ask it:
- Oregon handles this through a written disclosed limited agency agreement. It narrows the advice you get.
- A good answer:
- Raises it before you do and explains what changes.
39
What is your compensation, and how is it determined?
- Why ask it:
- Since August 2024 it must be stated specifically and conspicuously in a written buyer agreement before an MLS-participant agent tours a home with you.
- A good answer:
- A figure, in the agreement, presented as negotiable — because it is.
40
What happens if the seller offers less than what my agreement says?
- Why ask it:
- The gap is potentially yours to pay. Establish this before you tour, not at closing.
- A good answer:
- A clear mechanism, in writing.
41
How long is the agreement, and can I end it early?
- Why ask it:
- A short initial term lets you test the relationship at low cost.
- A good answer:
- Offers a short term or a genuine cancellation right without being pushed.
42
Do you receive a referral fee from anyone you are recommending?
- Why ask it:
- Legal and disclosable, but it does shape who gets recommended.
- A good answer:
- Answers plainly, either way.
7. Process and communication
BothCheap to ask, and the source of most of the frustration people report afterwards.
43
Will you be at the showings and the walk-through, or someone on your team?
- Why ask it:
- The person in the interview is not always the person who shows up — and in a building with a front desk and fob-controlled elevators, whoever attends needs to know the access rules.
- A good answer:
- Says clearly who does what, and that whoever attends has been in this building before.
44
How many clients are you working with right now, and any of them competing with me for the same building?
- Why ask it:
- Availability is a real constraint, and in a district this small two clients chasing the same stack is a genuine conflict.
- A good answer:
- A number, and a straight answer on overlap.
45
If a unit in my target line comes up, how fast can you get me in to see it?
- Why ask it:
- When three near-identical units in one building compete, the buyer who tours first sets the terms. Access in a secured Pearl building depends on the agent knowing its showing policy.
- A good answer:
- A time commitment, plus knowledge of the building's lockbox and front-desk rules.
46
Who else will I need — inspector, lender, escrow — and can you recommend condo-experienced ones?
- Why ask it:
- A condo inspection is not a house inspection. Oregon closes through escrow rather than an attorney, and a condo escrow has HOA payoffs and transfer fees a house does not.
- A good answer:
- Names people who work Pearl buildings routinely, and discloses any referral relationship.
Scoring the Interviews
You are not looking for the agent who answers every question. You are looking for the one who says “I don't know, here is how I would find out” where that is the honest answer, and who volunteers a problem before you find it.
Two answers carry more weight than the rest: which buildings they have closed in, and which Pearl buildings are difficult to finance. Both are hard to fake and neither can be learned from a script. If an agent cannot get the association to answer the last group, that is information about the building, not about the agent.
Where to Go Next
If you have not yet shortlisted anyone to interview, start with finding a buyer's agent or finding a listing agent. For the building-level diligence that follows, the condo buying guide covers HOA documents and reserves in more depth.