Rent Roll and Backgammon
Skill, Luck and Knowing when to Double or Drop.
Prepared by Damien Ingwersen, Senior Consultant, Adamson Legal Group | August 2026
The Rent Roll State of Origin series finished with a simple observation:
In rent roll transactions, as in State of Origin, the result often comes down to getting the selections right.
But once the selections have been made, another challenge begins. You still have to play the game.
And That Brings Us to Backgammon
Buying a rent roll has more in common with backgammon than might first appear. Both involve skill, judgment, calculated risk—and occasionally staring at the dice wondering what you did to deserve them.
A buyer cannot control everything. Landlords may change agents, key staff may leave and an apparently secure management may disappear shortly after settlement.
But, as any experienced backgammon player knows, blaming the dice only gets you so far. You cannot control what you roll. What you can control is the position you create before the dice are thrown.
For a rent roll buyer, that starts with the selections.
Setting Up the Board Properly
Which managements are genuinely valuable? Are the management agreements valid and transferable? Are the management fees sustainable? Are there arrears, disputes or unhappy landlords lurking beneath an impressive headline number?
Good due diligence is the equivalent of setting up the board properly.
A poorly investigated management is rather like leaving a blot exposed. You may get away with it—but you cannot complain when it gets hit.
Then There Is the Doubling Cube
In backgammon, knowing when to double, when to accept and when to walk away is part of managing risk. In a rent roll transaction, the equivalent may be deciding whether the price remains justified, whether the retention is adequate, or whether the risks identified during due diligence require the deal to be renegotiated or better to walk away.
A well-drafted retention mechanism recognises that some managements may disappear during the months following settlement and adjusts the price accordingly. A sensible restraint protects the goodwill without trying to turn the seller into a permanent spectator.
The lesson from both games is much the same.
First, get the selections right. Then play the position in front of you.
You cannot control the dice, just as you cannot control every landlord, employee or event after settlement.
But good players—and good rent roll buyers—do not depend upon luck.
They make their selections carefully; manage the risks they can control and arrange the board so that one bad roll does not bring the whole game undone.
Frequently Asked Questions
What does the backgammon analogy mean for buying a rent roll?
It illustrates that a rent roll purchase, like backgammon, combines skill and luck. Careful selection of which managements to buy and how the transaction is structured is the skill component; events after settlement — such as a landlord changing agents or key staff leaving — represent the element of luck a buyer cannot fully control.
What is meant by "setting up the board properly" when buying a rent roll?
It refers to due diligence. Before committing to a purchase, a buyer should establish which managements are genuinely valuable, whether the management agreements are valid and transferable, whether the management fees are sustainable, and whether there are arrears, disputes or unhappy landlords behind the headline number.
What happens if a management is poorly investigated before purchase?
A poorly investigated management is described as leaving a blot exposed — the risk may not surface immediately, but if it does, the buyer has no grounds for complaint, since the issue could have been identified during due diligence.
What is the "doubling cube" equivalent in a rent roll transaction?
It's the decision point during due diligence where a buyer weighs whether the price remains justified, whether the retention is adequate, or whether risks uncovered mean the deal should be renegotiated or abandoned altogether — similar to deciding whether to double, accept or walk away in backgammon.
Does settlement mark the end of the risk in a rent roll purchase?
No. Some managements may disappear in the months following settlement. A well-drafted retention mechanism accounts for this by adjusting the price if that happens, while a sensible restraint protects the goodwill purchased without preventing the seller from earning a living elsewhere.
What is the key lesson for rent roll buyers from the backgammon analogy?
First, get the selections right, then play the position in front of you. A buyer cannot control every landlord, employee or event after settlement, but by making careful selections and managing the risks that can be controlled, one bad roll doesn't have to undo the whole transaction.
This series is general commentary only and is not a substitute for legal, taxation or accounting advice on a particular transaction.