Saturday, August 15, 2026 / by Mike Shoaff
Why Experience Matters When Choosing a Realtor in Naples, Florida
What buyers and sellers should look for before choosing a Naples real estate agent
At 100% brokerages, the average real estate agent completes only about 1.25 to 1.75 transactions per year.
When I first heard that number, it really stood out to me.
Think about what that means if you are getting ready to sell your home. You could be interviewing an agent who has worked through only one or two actual transactions over the past year.
Now think about what you are asking that person to do.
You may be trusting them with a $500,000 home, a $1 million home or possibly one of the largest financial assets you own. You are expecting them to price it properly, market it, negotiate the contract, evaluate the buyer, manage inspections, watch deadlines, address appraisal or financing problems and guide the transaction all the way to closing.
That is a lot of responsibility.
I have always felt there is a big difference between having a real estate license and actually practicing real estate.
If an agent sold one home last year, how much hands-on experience did that agent really gain? How many offers did they negotiate? How many inspections did they work through? How many appraisal issues, insurance problems, financing complications, title questions or difficult negotiations did they actually encounter?
These are questions I think buyers and sellers should be asking.
I Believe in the 10,000-Hour Rule
I was always told about the “10,000-hour rule.” The basic idea is that it takes roughly 10,000 hours of practice and real-world experience to become highly skilled at something.
I believe there is a lot of truth to that.
After working through hundreds of real estate transactions and contracts, I have surpassed that benchmark several times over.
And here is the interesting part: I am still learning.
I learn something new in this business all the time. That is one reason I put so much value on actual experience.
You can read every real estate book you can find. You can take classes, attend seminars and watch educational videos. I do those things too, and education is important. But there is no substitute for sitting at your desk with a real contract in front of you and a real problem that needs to be solved.
Do that hundreds of times and you start seeing things differently. You recognize problems earlier. You know which questions to ask. You know when something in a contract deserves a closer look. You begin to recognize when an offer that looks great on the surface may actually have weaknesses.
You also learn what not to do. Sometimes the transactions that give you the biggest headaches are the ones that teach you the most.
Real Estate Has a Way of Throwing Curveballs
I wish I could tell every seller that once we get their home under contract, everything is going to be easy. That simply is not how real estate works.
Some transactions are straightforward. Everything lines up, everyone does what they are supposed to do and we get to closing without much drama.
Then there are the others.
An inspection uncovers something nobody expected. The appraisal comes in low. The buyer’s lender suddenly has a problem. An insurance issue appears. Something comes up with the title. A condominium association needs additional documentation. A deadline gets missed. A buyer gets nervous three weeks into the transaction.
I have seen plenty of situations where something happens that nobody expected when the contract was signed.
In Naples, we have another layer of issues that agents need to understand. Flood zones and elevation matter. Insurance matters. Condo reserves and special assessments matter. Milestone inspections matter. HOA requirements matter. Wetlands can be extremely important with vacant land.
The contract itself matters.
This is where experience starts paying dividends. A good Realtor in Naples, Florida should not just know where the blanks are on a contract. They need to understand what those terms mean when something goes wrong.
Getting an Offer Is Only the Beginning
When I meet with sellers, a lot of the conversation naturally revolves around marketing. How are you going to market my home? Where will it be advertised? What should we list it for?
Those are important questions. But there is another question that I think is just as important:
What happens when we get an offer?
That is when another part of my job begins. I have to look beyond the price at the top of the contract.
How is the buyer paying? How much money are they putting into escrow? What contingencies are included? How long is the inspection period? Is there an appraisal contingency? Does the buyer need to sell another property? How strong is the financing? What are the ways this buyer could potentially get out of the contract?
Those details matter.
I have seen situations where the highest offer was not necessarily the best offer. Give me a slightly lower cash offer with strong escrow and fewer contingencies versus a higher offer loaded with contingencies, and we may have a very different conversation about which one is actually better for the seller.
That is where working through hundreds of contracts makes a difference. You learn to look beyond the big number at the top.
Naples Is Not One Real Estate Market
This is another thing I explain to buyers and sellers all the time: there really is no single “Naples real estate market.” Naples is a collection of many smaller markets.
What is happening with beachfront condos in Park Shore may have very little to do with what is happening with acreage homes in Golden Gate Estates.
A bundled golf community is different from a non-golf community. A condominium west of U.S. 41 can have completely different considerations from a newer single-family home in North Naples. Sometimes two communities only a few miles apart are moving in completely different directions.
This is why I spend so much time looking at the details. I look at sold properties, but I also want to know what is currently for sale. What has gone pending? What has been sitting? Which sellers are reducing their prices? What expired without selling? Most importantly, why?
A knowledgeable real estate agent in Naples, Florida needs to do more than pull three comparable sales and average the prices.
Flood zones, elevation, insurance, HOA fees, condominium fees, reserves, assessments, roof age, building age, location, amenities, golf membership requirements, wetlands and even the specific section of a community can affect value.
The numbers are important. Knowing how to interpret the numbers is even more important.
You Can Often See a Market Changing Before the Statistics Catch Up
I have always been a numbers person when it comes to real estate. I look closely at inventory, pending sales, closed sales, days on market, expired listings, price reductions and the difference between asking prices and actual selling prices.
But there is another part of understanding a market that is difficult to put on a spreadsheet. It is what you are seeing and hearing every day.
When buyers suddenly become more aggressive with offers, I notice it. When listings start sitting longer, I notice it. When I see more price reductions in a particular community, I notice it. When buyers who were competing for properties six months earlier suddenly have five similar homes to choose from, that changes the conversation.
An active agent gets to see those changes happening in real time. The official statistics eventually tell the story, but sometimes you can see the story developing before the statistics fully reflect it.
That firsthand knowledge is extremely valuable when I am helping a seller decide how to price a home or helping a buyer determine what to offer.
What Do Real Estate Awards Actually Tell You?
Over the years, I have been fortunate to receive multiple RE/MAX Platinum Club Awards, the RE/MAX Lifetime Achievement Award, RE/MAX Hall of Fame recognition, RealTrends Verified recognition and numerous other production and achievement awards.
I am not mentioning these to fill a page with trophies. There is a reason I think they are relevant to this particular discussion.
Production awards represent transactions.
Behind those awards are listings, buyers, contracts, negotiations, inspections, problems, solutions and closings. For me, that is what matters.
The awards provide another way for someone considering hiring me to verify that I am actively doing the job. There is a big difference between having a real estate license hanging on the wall and actively working through real estate transactions.
Ask Your Agent How Many Transactions They Actually Do
If I were hiring someone to sell my own home, I would want to know: How many transactions did you complete last year?
Not how long have you had a license. Not how big is your company. Not how many agents are in your office.
How many actual real estate transactions did you personally work through?
I would also want to know whether the agent understands my particular type of property.
If I am selling a Naples condominium, does the agent understand condo reserves, assessments, insurance, milestone inspections and the other issues affecting condos?
If I am selling acreage in Golden Gate Estates, does the agent understand wetlands, DEP reports, flood zones and how those factors affect land value?
If I am selling in a golf community, does the agent understand how membership requirements can affect the buyer pool and marketability?
That local knowledge matters.
Do Your Homework Before Hiring a Real Estate Agent
I encourage buyers and sellers to research me before they hire me. I think you should research any other agent you are considering too.
Look at their sales history. Read their reviews. Look at their production and professional recognition. Then talk to them.
Ask questions. How many transactions have you recently completed? What is happening in my neighborhood? What are the competing properties? What are buyers actually paying? What problems do you see with my property? What would you do if the appraisal came in low?
If you are interviewing someone to list your home, ask them to explain the comparable sales to you. Do not just look at the pretty presentation. Make sure the agent understands the numbers behind it.
If someone is going to tell you what your home is worth, they should be able to explain exactly how they arrived at that number.
You could be making a decision involving hundreds of thousands or millions of dollars. Choosing the best real estate agent for your particular situation deserves some homework.
Experience Matters Most When Something Goes Wrong
After working through hundreds of contracts and real-life real estate situations, one thing I know for certain is that there is always something new to learn.
No two properties are exactly alike. No two buyers are exactly alike. And no two transactions are exactly alike.
I cannot promise a seller or buyer that nothing unexpected will happen during a transaction. Nobody can.
What I can bring to the table is the experience gained from working through hundreds of transactions and seeing many of those unexpected situations before.
You start developing instincts. You know when something does not look right. You know when you need to ask another question. You know when a deadline is more important than it may appear. You know when an offer deserves a closer look.
That comes from repetition and real-world experience. It goes back to the 10,000-hour rule I mentioned at the beginning.
The more you actually do something, the better you become at recognizing the little things that can eventually become big things. In real estate, those little things can sometimes involve a lot of money.
Real estate is too important to have someone learning the business on your transaction.
Looking for an Experienced Realtor in Naples, Florida?
With more than 20 years of Southwest Florida real estate experience, Naples Realtor Mike Shoaff with RE/MAX Hallmark Realty helps buyers and sellers navigate pricing, offers, inspections, negotiations and closing throughout the Naples area.
Whether you are buying or selling a condominium, single-family home, golf-community property, waterfront residence or acreage property, you will work directly with Mike from the initial conversation through closing.
Mike Shoaff, REALTOR®
RE/MAX Hallmark Realty
Cell: 239-298-9903
