Most expensive real estate mistakes don’t come from bad intentions — they come from rushed decisions.
I see it all the time. People feel pressure to “do something,” even when they’re not fully clear on what they actually want or need.
Lately, I’ve noticed more clients using AI tools as a way to slow down and think through decisions before committing to them. Not to replace professional advice — but to ask better questions upfront.
I actually think that’s a good thing.
Before you buy, sell, remodel, or decide to wait, clarity can save you money, time, and stress. Here are five AI-style prompts that can help you think things through more clearly before making a move.
1. “Help me compare staying put versus moving within the next two years.”
This prompt encourages you to zoom out and see the full picture.
Instead of fixating on whether now is the "right time" to move or whether rates are favorable, it asks you to consider everything at once: your lifestyle, your finances, your timing, and what actually matters to you over the next couple of years.
Staying put might mean lower upfront costs, less disruption, and more financial predictability. But it could also mean outgrowing your space, delaying a change that would genuinely improve your life, or spending money on a home that still doesn't quite work for you.
Moving might offer a better long-term fit — more space, a shorter commute, a neighborhood that aligns with where you are now. But it comes with transaction costs, adjustment periods, and the complexity of timing a sale and purchase.
The value of this question isn't that it gives you a definitive answer. It's that it forces you to look at the tradeoffs side by side — so you're making a decision based on what's true for your situation, not just reacting to external pressure or a sense that you "should" do something.
2. “What costs am I likely underestimating if I buy a home right now?”
Most buyers focus heavily on the purchase price and monthly mortgage payment — and understandably so. Those are the biggest, most visible numbers.
But this question pushes you to think about everything else: ongoing maintenance, unexpected repairs, property tax increases, homeowners insurance (which has risen significantly in many areas), higher utility costs, HOA fees, landscaping, furnishings, and future upgrades or improvements.
It also surfaces opportunity costs — what else that money could be doing if you waited, invested differently, or stayed flexible for another year.
In real estate, the financial surprises rarely come from the big, obvious expenses. They come from the smaller, recurring costs that add up over time — and from underestimating how much a home will actually require in the first few years.
This isn't about talking yourself out of buying. It's about going in with open eyes, a realistic budget, and enough cushion to handle what comes up without stress or regret.
3. “If I remodel instead of move, what should I think about from a livability and resale perspective?”
This is one of the most common crossroads homeowners face — and one of the easiest places to make an expensive mistake.
A remodel can absolutely be the right move. But this question helps you figure out whether it actually solves the core problem — or just addresses a surface-level symptom.
From a livability perspective, you want to ask: Will this renovation genuinely improve how we live day-to-day? Does it fix the thing that's actually bothering us — or are we spending money on something cosmetic while the real issue (lack of space, poor layout, neighborhood fit) remains?
From a resale perspective, you want to think about whether the improvements make sense for your neighborhood and price point. Are you over-investing in features that won't hold their value? Are you creating something so personal or niche that it might actually narrow your buyer pool later?
This kind of reflection can prevent you from spending $75,000 on a kitchen remodel only to realize six months later that you still don't have enough bedrooms, the commute still doesn't work, or the home fundamentally doesn't fit your life.
Sometimes a remodel is exactly right. Sometimes it's just delaying an inevitable move. This question helps you figure out which one you're looking at.
4. “What does ‘waiting a year’ actually cost me — financially and emotionally?”
Waiting often feels like the safest option. Sometimes it genuinely is.
But this question helps you understand what delay actually means — so that if you choose to wait, it's an informed decision rather than avoidance or paralysis.
Financially, waiting might mean rent increases, missed equity growth, or rising construction costs. Emotionally, it could mean ongoing frustration, lack of space, or staying in a situation that no longer fits your life.
On the other hand, waiting might give you time to save more, clarify what you want, or let the market settle. The point isn't to push action — it's to weigh the tradeoffs clearly so waiting becomes a conscious choice, not just a default one.
5. “What questions should I be asking before I decide to buy or sell?”
This is my favorite prompt — and the one I think is most valuable.
It shifts you out of decision mode and into reflection mode. Instead of rushing toward an answer, you pause to consider what information you might be missing, what assumptions you're making, and what actually matters to you beneath the noise.
Often, people jump straight to "Should I buy?" or "Should I sell?" without first asking things like: What problem am I trying to solve? What would success actually look like a year from now? What am I optimizing for — space, cost, commute, schools, flexibility? What risks am I willing to take on, and which ones would keep me up at night?
This question doesn't give you the answer. It helps you find the right questions — the ones specific to your situation, your priorities, and your life stage.
And more often than not, the smartest move doesn't become clear until those questions are on the table. Sometimes the answer is to act. Sometimes it's to wait. Sometimes it's to reframe the problem entirely.
But you can't make a good decision until you know what you're actually deciding.
A quick word of caution
AI tools can be helpful for organizing thoughts and exploring scenarios — but they are not infallible. I’ve personally seen AI get things wrong, miss local context, or oversimplify complex situations.
And importantly, AI doesn’t know your neighborhood, your street, or your local market dynamics.
These tools don’t replace realtors, lenders, inspectors, or other professionals. They can’t walk a home, spot red flags, understand hyper-local pricing, or factor in nuances that only experience brings.
Think of AI as a brainstorming assistant — not a decision-maker.
Final thought
Whether you use AI or not, the real value comes from slowing down and thinking clearly before making a move.
The right questions — asked early — can save you far more than chasing the “perfect” rate or timing the market just right.
If you’re considering buying, selling, remodeling, or deciding whether to wait, I’m always happy to talk it through. No pressure. No rush. Just an honest conversation about what makes the most sense for you.
