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Investment Lesson

The Investor Who Waited Too Long

He watched the market for nine years. The market watched him back, and kept rising.

4 min readNovember 10, 2025Investment LessonsTamarindo

He first walked Tamarindo’s beach road in 2015 with a folder of listings and a feeling that prices had gotten ahead of themselves.

He decided to wait for the correction.

He was patient. Disciplined, even. He rebuilt the folder in 2017 — higher. Again in 2019 — higher still. Each visit, the entry point he’d passed on had quietly become the good old days.

Then 2020 arrived, and for one strange season he was right: the world stopped, and a real window opened. But windows like that never feel like opportunities at the time; they feel like the end of the world, which is the price of admission. He waited for clarity instead. Clarity came — attached to a stampede of remote workers who repriced the entire coast within eighteen months.

The dip he’d waited nine years for lasted about nine months, and required more courage than any market he’d declined to buy.

“I wasn’t waiting for a price,” he admits now. “I was waiting for certainty. There’s no listing for that.”

He finally bought in 2024: a smaller unit than the 2015 folder would have gotten him, at multiples of the price, in a market that had stopped apologizing for itself. Prime coastal supply is finite — the towns are hemmed by parks, mountains, and maritime law — and finite things, over a decade of growing demand, mostly go one direction.

It rents well. It has already appreciated. He’s glad he bought it, and precise about the accounting: gladness, minus nine years.

“I wasn’t waiting for a price. I was waiting for certainty. There’s no listing for that.”

The Story Timeline

2015First folder of listings — 'overpriced'
2019Still waiting. Still rising.
2020The window — disguised as a crisis
2022Repriced coast, eighteen months flat
2024Finally bought. Smaller. Higher. Happy-ish.

The Cost

A decade of appreciation observed, not owned
Rent paid to other people's assets, 9 years
The compounding he watched from the sidelines
Certainty: permanently out of stock

Lessons For Future Buyers

01Time in market beats timing itEspecially in finite, supply-capped coastal towns.
02Define criteria, then act when metA written checklist converts fear into a decision.
03The dip never feels like a dipReal windows arrive dressed as bad news.
04Scarcity has a directionParks, mountains and maritime law cap this coast's supply.
05Waiting has a price tag tooCount the rent, the appreciation, and the years honestly.

Insider Perspective

We are not the 'prices only go up' people — markets breathe, and we've told clients to walk away from plenty. But the waiting strategy needs an honest ledger: on this coast, the decade's patient observers paid more than its imperfect buyers.

JSJames SimmonsFounder, Costa Rica Property Insider

Where They Are Now

His advice to the 2015 version of himself fits on a napkin: 'You're not early. You're already late. Buy the good one and hold it.'

Considering Tamarindo? You can read the unfiltered local take on this area, or talk it through with us before you fall in love with anything.

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