I Don’t Love High-Yield Properties. I Love Properties With Multiple Ways to Win.

Win by simply holding. Win even more if you act. And after moving to the Netherlands, I realized I needed a sixth investment principle: “easy to hold.”

In my previous article, I wrote about a property in Fujiyoshida that I decided not to buy.

The original asking price had been around:

¥10 million.

Then it dropped to:

¥4 million.

And during the site visit, I even asked:

“What about ¥1 million?”

The numbers looked interesting.

The single-story residential section could potentially be rented out.

The former shop section also had several possible uses.

And if the total investment could be kept around ¥5 million, the projected yield looked very attractive.

Still, after thinking about it overnight, I decided:

PASS.

While writing about that decision, another question came to mind.

Why did I still feel that the property was so close to being something I wanted?

It had an uncertain water route.

Roof leaks.

Rust on the steel frame.

A large amount of belongings to remove.

And rebuilding restrictions.

Normally, I could have simply said:

“Too much trouble.”

But I kept thinking about it.

And I realized why.

It had a lot of cards to play.

I Don’t Actually Love High Yield for Its Own Sake

Of course, yield matters.

But what I really like is not a property where there is only one way to win.

For example:

A normal residential lease produces a 15% yield.

That alone may already be enough.

But perhaps converting it into short-term accommodation could push the return above 20%.

Maybe I could operate my own business there someday.

Maybe I would enjoy using it myself.

Maybe a neighboring property could become available.

Maybe a road expansion or redevelopment project creates unexpected upside.

And, of course, I could always sell.

What I really like is this:

Even if nothing happens, I am already winning.

And:

If something happens, I can win even more.

That is the kind of property I enjoy owning.

The Important Part Is That I Don’t Have to Play Every Card

A property might offer several possible strategies:

Long-term rental.

Short-term accommodation.

Retail.

Office.

Storage.

Personal use.

Change of use.

Acquiring neighboring lots.

Land consolidation.

Redevelopment upside.

Sale.

But I do not need to pursue all of them.

That is actually the point.

If long-term rental works well enough, I can simply keep renting it.

If short-term accommodation becomes attractive later, I can consider that.

If I want to start a business one day, perhaps I can use the commercial space.

If the property next door comes onto the market, I can decide whether to buy it.

So my ideal structure is:

The base case already works, while several upside cards remain available.

I can wait.

I can choose.

I can act only when I want to.

That freedom is valuable.

I Enjoy Properties With Multiple Futures

Maybe that is why I enjoy real estate so much.

For me, a property is not just:

“An asset yielding X%.”

It can have many possible futures.

A home.

A rental.

A minpaku.

A shop.

A warehouse.

A family base.

A future development site.

A piece of land that might eventually combine with neighboring lots.

I enjoy thinking:

“Maybe I will use this part differently in five years.”

“What if the property next door becomes available in ten years?”

“What if this area changes?”

The fact that I do not need to decide immediately makes it even more interesting.

The value is not only in what the property is today.

It is also in the number of reasonable choices it may give me later.

But There Is a Difference Between an “Option” and “Homework”

The Fujiyoshida property taught me something else.

Having many possibilities is not enough.

Some things look like options, but they are actually obligations.

For example:

“Someday I could turn the shop into an event space.”

That is an option.

I do not need to do it now.

I can wait until I have the time, money and reason to do it.

But:

“The roof is leaking, so I need to repair it.”

That is not an option.

That is homework.

The same applies to:

The water route must be clarified before renting.

The belongings must be removed before the property can be used.

The steel frame may require inspection.

The deteriorated exterior may need attention.

These are things the property starts demanding from me the moment I own it.

And that distinction matters.

I do not want:

a property with many things to do.

I want:

a property with many things I could choose to do.

Those are very different.

So the Value of Optionality Is Not Just the Number of Options

I have started thinking about it this way.

The value of a property’s options depends on at least three things:

How many cards exist.

How powerful those cards are.

How cheaply and easily I can play them.

Imagine two properties.

Property A has ten possible future uses.

But every option requires another ¥5 million investment and months of work.

Property B has only three options.

But all three can be activated cheaply and gradually.

I may prefer Property B.

Optionality is not simply:

more possibilities = better.

What matters is:

more useful possibilities with low pressure and low activation cost.

The Fujiyoshida Property Actually Had a Lot of Good Cards

This is why the property was so tempting.

The flat single-story residential section had real potential.

First option:

Normal long-term rental.

That may have been the most sensible strategy.

Given the surrounding residential environment and the number of elderly neighbors, I became less convinced that short-term accommodation should be the first choice.

But the short-term accommodation card still existed.

So:

Long-term rental first.

And perhaps:

Minpaku later.

Then there was the former shop section.

At first, it did not need to become anything special.

It could simply be:

Storage.

Later, if the property was performing well and I had more time and budget, the shop could potentially become:

An event space for guests.

A karaoke room.

A party room.

A space where larger groups could enjoy spending time together.

Of course, actual operation would require checking zoning, fire-safety requirements, noise issues and relations with neighbors.

But as a concept, there were several paths.

And then there was the surrounding area.

There were several old properties nearby.

Some appeared difficult to rebuild.

There was also a house across the road that could perhaps become interesting one day.

Over ten or twenty years, maybe one property becomes available.

Then another.

Perhaps several parcels could eventually be combined.

If that happened, the original property could become something very different.

That kind of long-term optionality is exactly the sort of thing I enjoy.

So principle number two—

“Multiple upside options”

—was actually one of this property’s strengths.

The problem was not the lack of options.

The problem was the amount of work required before I could enjoy them.

I Realized I Already Had Five Investment Principles

While thinking about this, I started writing down what my favorite properties tend to have in common.

I realized there were five principles I had already been using, even if I had never written them clearly.

And then this Fujiyoshida property added a sixth.

Principle 1: The Base Case Works by Itself

The most boring strategy should already make sense.

If normal residential leasing works, that is enough.

I do not want to rely on:

“Minpaku must succeed.”

“Redevelopment must happen.”

“The neighbor must sell.”

“The market must rise.”

I want the investment to survive without the exciting story.

The base case should already work.

Principle 2: There Are Multiple Upside Cards

Once the base case works, I want optionality.

Short-term accommodation.

Retail use.

Personal use.

Change of use.

Neighboring acquisitions.

Land consolidation.

Redevelopment.

Sale.

The more reasonable upside paths I have, the more interesting the property becomes.

But only after the base case works.

Principle 3: I Am Not Forced to Play Those Cards

This is one of the most important principles.

I do not want:

“Run minpaku or lose money.”

I prefer:

“Long-term rental works. Minpaku is optional.”

I do not want:

“Renovate the shop immediately or the property becomes unusable.”

I prefer:

“The shop can remain storage for five years, and I can improve it when I want.”

The timing should belong to me.

Options should create freedom, not pressure.

Principle 4: Time Works in My Favor

I like properties where waiting itself has value.

Maybe a neighboring property becomes available.

Maybe a leasehold structure changes.

Maybe an old building is returned.

Maybe a district improves.

Maybe land can eventually be combined.

Maybe new uses become possible.

In that kind of investment:

time creates optionality.

Of course, buildings also age.

So I do not want the negative effect of time—deterioration and maintenance—to overwhelm the positive effect.

Ideally:

I can wait comfortably, and waiting may create more choices.

Principle 5: Owning It Is Enjoyable

Not every part of my real-estate decision is financial.

I like properties I enjoy owning.

Maybe I want to stay there.

Maybe I enjoy thinking about future uses.

Maybe I enjoy the neighborhood.

Maybe the relationships around the property become part of the value.

I like properties where I can think:

“I would be happy to keep this for a long time.”

Not:

“I need to sell this as soon as possible.”

And then this Fujiyoshida property revealed principle number six.

Principle 6: It Must Be Easy to Hold

This is the new one.

And I think it became much more important after moving to the Netherlands.

If I were still living in Japan, I probably would have bought the Fujiyoshida property.

I actually like this kind of project.

Clear out some belongings this weekend.

Clean another room next weekend.

Paint a wall.

Think about what to do with the shop.

Leave part of it unfinished for a while.

Spend one or two years gradually improving the place.

That sounds enjoyable to me.

But remote ownership changes the meaning of the same work.

“I will clear it out.”

becomes:

“I need to find someone to clear it out.”

“I will fix that.”

becomes:

“I need to get quotes, compare contractors and decide remotely.”

“I will stop by and check it.”

becomes:

“I need someone to send me photos and explain what is happening.”

Something that would have been a hobby if I lived nearby becomes:

remote management.

And the cost is not only money.

It is:

My time.

My family’s time.

Mental bandwidth.

Attention.

Decision fatigue.

So now I need to ask:

“Can I own this property easily?”

Can it operate without constantly demanding my attention?

Can it be managed remotely?

Can I leave it alone for periods of time?

Can I own it without sacrificing too much family time?

That has become a real investment criterion.

That Also Explains Why I Like My Naha Investments

When I think about my properties in Naha, the structure suddenly makes more sense.

I can simply rent them out.

And that is fine.

I do not need to force another strategy.

I can hold them.

If nothing changes:

I am still okay.

But over time, something may happen.

A leased building may eventually be returned.

The land may become easier to use as one parcel.

Another use may become possible.

The surrounding area may change.

But none of those things need to happen for the investment to work today.

That is the structure I like.

If the leasehold is never returned, I can still win.

If it is returned, I may win more.

And importantly:

I can wait.

I am not being forced to act.

That is powerful.

So How Did the Fujiyoshida Property Score Against the Six Principles?

Looking back, I would rate it roughly like this.

1. The base case works by itself: △ to ○

The residential portion could probably work as a normal rental at the right acquisition price.

But too many assumptions remained around water, repair costs and cleanup.

2. Multiple upside cards: ○

This was one of its strengths.

Long-term rental.

Minpaku.

Storage.

Event space.

Large-group use.

Potential acquisition of neighboring properties.

There was real optionality.

3. I am not forced to play the cards: ×

This was weak.

Water.

Leaks.

Belongings.

Steel-frame condition.

Some issues would have demanded action almost immediately.

4. Time works in my favor: △ to ○

The neighboring-property story could become interesting over a long period.

But the existing buildings would also continue to deteriorate.

Time created both upside and cost.

5. Owning it is enjoyable: △

If I lived in Japan, this would probably be an ○.

In my current situation, much of that enjoyment would turn into remote coordination.

6. Easy to hold: ×

This was the biggest issue.

For my current life, the initial and ongoing management burden was too high.

And that is why I passed.

Not because it was a bad property.

Actually:

It was very close to being exactly the kind of property I like.

That is what made it difficult.

I Now Know More Clearly What I Want to Buy

This site visit changed the way I will evaluate properties going forward.

What I want is something that:

Works in the base case.

Has several upside cards.

Does not force me to play those cards.

Lets time work in my favor.

Is enjoyable to own.

And:

is easy to hold.

High yield is useful.

But it is only one outcome.

I may even prefer a slightly lower-yield property if these six principles are much stronger.

Because I do not think real-estate investing is a game of predicting:

the one future where you make the most money.

I think it is closer to:

building a position where you are okay across many possible futures — while keeping several large upside options available.

That is the kind of investing I like.

What I Brought Home From the Site Visit

I did not buy the property.

But I do not think the trip was wasted at all.

In fact, it may have been more valuable than buying something.

Because I came home understanding my own investment philosophy better.

Moving to the Netherlands changed my life.

And because my life changed, my investment principles changed too.

Five principles became six.

The new one is:

“Easy to hold.”

From now on, I want properties where:

I win by simply holding.

I can win more if I choose to act.

I do not need to rush.

And most importantly:

I can keep owning them comfortably.

I did not buy the property in Fujiyoshida.

But I brought something home with me.

I bought one more investment principle.

And that alone made the site visit worth it.

Japan Working Home™

For me, the ideal Japan Working Home™ follows the same logic.

A property that works in a simple base case.

A place that can generate income when I am away.

A place I can use myself.

A property with several possible futures.

And a property that does not become a burden simply because I own it.

Win by holding.
Win more by acting.
And stay free enough to choose.

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