Eddie Dilleen is one of Australia’s biggest residential landlords. He reckons he now has 200 properties in his portfolio.

But he just bought perhaps his favourite house yet. More than 25 years after his parents divorced and sold the family home for $97,000, he has purchased it back for a bit under $1 million.

“I just bought it sight unseen,” he told Yahoo Finance.

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Dilleen said he has spent the past decade periodically checking if the house had returned to market.

“You can set reminders and stuff like that, but when I was on my phone messing around, I would randomly check it literally every one or two weeks for the past 12 years.”

His parents first bought the home in the far western suburbs of Sydney in 1985 for $51,000. When he saw it listed, he felt “an overwhelming rush of excitement,” he said.

“This home holds some of my best memories… and some tough ones too. But today, it represents something completely different,” he wrote online, sharing a photo of himself next to the sold sign on Tuesday. “It’s proof that where you start doesn’t define where you finish.”

He ultimately bought it for 19 times what his parents paid for it 41 years ago.

“The affordable properties and suburbs, they usually grow at a higher percentage value. I’m all about percentages,” he told Yahoo Finance.

“Everyone talks about the best, blue chip locations, but I buy everywhere.”

Dilleen, who is in his mid 30s and also runs a buyers agency and writes books about real estate investing, estimates the properties he owns are now collectively worth about $150 million (he likes to buy blocks that contain multiple units) with about $60 million in debt against that.

According to ATO data, he is about one of 166 mega landlords who own 20 or more rental properties in their own name. Dilleen said he owns “about 30 or 40” in his own name, and others through trust and company structures.

Landlords overly reliant on negative gearing ‘will be wiped out’

With less than two weeks until the Labor government hand downs its promised “ambitious” budget, property investors are bracing for possible changes to the rules around tax deductions related to investments.

One of the most commonly used is negative gearing, which allows landlords to claim losses to reduce the amount of income tax they pay. But its days could be numbered with the federal government expected to cap, or possibly even scrap, the existing policy under certain circumstances. While no announcements have actually been made, most observers expect such a change to be grandfathered in for existing investors.

Dilleen says he “couldn’t care less” if the government does away with negative gearing because he tries to focus on purely “undervalued” assets that have good rental return, although he admits he takes advantage of it on some of his properties.

“Just some of my properties are negatively geared, but many of them are not,” he said.

“But it is a big thing for the average person that owns one or two properties.

“Average people, investors starting out that are just getting started buying properties, many of them rely on negative gearing, but that is a stupid strategy.”

Dilleen pointed to sections of the market, often inner city locations, where houses can cost $2-3 million but have relatively weak yield, or rental income, compared to the sale price.

“That’s stupid, because if they are negatively gearing like a $3 million house, and then you’re getting $1,000 a week renting it out, they’re going to be in big trouble. They’re silly investors … they’re relying on negative gearing and a lot of them will get wiped out,” he said.

According to the latest figures from the ATO, about half of all investment properties are negatively geared.

There are 1.1 million negatively geared property investors, out of a total of 2.26 million. In terms of total stock, of the 3.2 million property interests held by individual taxpayers, 1.59 million or 49.4 per cent are negatively geared.

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Financial services companies are “far ahead of regulators in adoption and deep adoption of AI,” said the report issued Tuesday (April 28) by the Cambridge Centre for Alternative Finance.

“The scale and pace of AI adoption in financial services is genuinely remarkable – 4 in 5 firms are already deploying AI at some level, agentic systems have crossed into the mainstream and real productivity and profitability gains are being felt across the industry, although unevenly,” said Bryan Zhang, the center’s executive director.

As for regulators, 48% of the regulators surveyed said they were “still in the ‘exploring’ stage for AI adoption” or not engaged with AI at all.

The report found that software engineering is the “most mature” AI application in the financial sector and is a primary cyber risk transmission vector, with 48% of respondents flagging adversarial AI as a primary concern.

The center said this is underlined by Anthropic’s claim that its Mythos model is often more capable than humans when it comes to hacking, which makes manual oversight of AI use in financial services problematic, the center added.

Complicating matters is a “notable perception gap,” the report said. AI vendors put less emphasis than industry and regulators on adversarial AI threats, something mentioned by 50% of industry respondents and 57% of regulators, but only 35% of vendors.

The same held true for the issue of cyber/operational resilience: 32% of vendors mentioned it, compared to 46% for industry and 59% among regulators.

“These intersecting vulnerabilities can also feed into the top perceived risk across all stakeholders – data privacy and protection (73% of respondents) as sensitive data is typically the primary target for the cyber exploits these vulnerabilities enable,” the report added.

In related news, PYMNTS wrote Tuesday about increasing levels of AI adoption among retailers as AI agents play a greater role in commerce.

“Agentic artificial intelligence’s first real test in commerce may come not as a flashy shopping tool, but as a trust exercise that could decide who leads the next phase of digital payments growth,” the report said.

PYMNTS Intelligence research shows that 45% of consumers would be comfortable letting AI agents complete purchases on their behalf, while 43% of retailers are piloting autonomous AI.

The research found that 95% of consumers report at least one concern about agentic commerce, with half saying they would trust agentic commerce more if they knew fraud protections were in place.

First home buyer Jessica Ricci was just trying to save a little extra money through her superannuation in a federal government scheme intended to help people like her. But an error from tax authorities has left her paying more tax than the top income bracket on some super contributions – ironically having the exact opposite of the intended effect of the policy.

As a result, she’s lost out on an extra $2,250 in savings that was supposed to go to her house deposit. While the ATO pushed back over who was at fault for the mix-up, her case has highlighted an increasingly problematic blindspot when it comes taxpayers getting the short end of the stick when dealing with tax authorities.

“I’m definitely feeling a little bit helpless,” she told Yahoo Finance. “There’s not a clear path to rectify this.”

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Jess was tipping extra money into her superannuation as part of the First Home Super Saver Scheme which has been running for years and allows eligible first home buyers to take advantage of the tax benefits of their retirement savings and then pull those extra contributions out to use for a house deposit.

As part of the scheme, individuals need to apply to the ATO, which in turn requests the related money from the person’s super fund.

Over four years, Jess contributed the maximum $50,000 amount, ensuring not to exceed the $15,000 yearly cap. She did so with the expectation of claiming the benefit at the time of her house purchase, as per the rules of the scheme.

When she went to make the claim, much of the information was auto-populated by the ATO website. And after receiving her funds, and the amount being less than expected, she soon discovered that her first contribution was wrongly classified as a concessional contribution, meaning $2,250 was, in the words of an ATO official, “retained by the ATO as withholding tax”.

She has spent months going back and forth with tax officials trying to get the money she believes should be owed to her.

“They’ve all taken the same stance, which is; ‘Well, yeah, we made a mistake, but you didn’t catch it. You said that what we provided you was fine, so it’s your fault’.

“I think it’s crazy to put the onus or the burden on the average person. I think most people would rightfully assume that pre-filled data provided by the ATO would be accurate,” she said.

“If I made a mistake on my tax return that benefited me, I’d be expected to fix it. But when the system made a mistake that benefits the ATO, it seems that there’s no direct pathway to correct it, which is really frustrating.”

ATO officials insisted Jess’s only recourse was to file a complaint with the federal Tax Ombudsman, which she did.

However, after “a thorough review” there was nothing that could be done to undo the error.

“FHSSS only allows for one release. This is why it is important that the person, lodging the request, ensures the information is correct at the time it is lodged,” the ombudsman said in a statement to her.

“Regretfully, I am unable to amend the amount released to you at this time.”

‘I worked three jobs to save my house deposit’

While the $2,250 that she has lost out on hasn’t been make or break for her situation, she said that kind of money could be crucial for someone scrapping together a house purchase.

“I worked three jobs to save my house deposit, I worked incredibly hard. And for some people, it actually would be the difference,” she said.

“I was doing all kinds of things to maximise the opportunity to save and to get myself into my first home.”

In a video on social media this month, the Melbourne resident shared her “incredibly frustrating” saga as a warning to others.

“On the $15,000 contribution I made that financial year, I’ve now paid 47.5 per cent tax, which is more tax than the maximum tax bracket that exists,” she said.

Tax accountant calls out ATO over ‘widespread’ errors in pre-filled data

As the tax office increasingly relies on data matching, the root problem of incorrect information being pre-filled into ATO systems has become much more “widespread” and problematic, tax accountant Belinda Raso says.

“It’s something that we’ve seen a lot,” she told Yahoo Finance. “It could be employment information, it could be the first home buyer Super Saver scheme, it could be bank interest, anything at all.”

Raso said in some cases, even if the taxpayer does spot the error and changes it at the time, the ATO’s data matching can subsequently override it and revert back to the incorrect information at a later date.

“Unless you get that information changed by the person or institution that’s responsible for that information, they’ll still keep going back to it,” she said.

The accountant said the growing reliance on “AI and data matching” means there needs to be a better form of recourse for taxpayers who are caught out by incorrect data being automatically input.

“If they’re going to have this pre-filled information on your return, for taxpayers we need to have some kind of mechanism,” she said. “Because the ATO is putting their hands up in the air, the Ombudsman’s putting their hands up in the air, and it’s up to taxpayers to then go; ‘Well look, this is wrong’.”

ATO says ‘no mechanism’ to fix the superannuation mistake

Jess’s superannuation fund confirmed they provided the correct information to the ATO.

In a statement to Yahoo Finance, the ATO admitted “there is no mechanism” to rectify such a mistake once funds have been released through the scheme.

“When individuals request a FHSS determination, ATO systems will pre-fill information for the individual,” an ATO spokesperson said. “The determination application form allows individuals to delete or vary any of the pre-filled information, as well as add new information where appropriate. Any information adjusted or provided by the individual can impact the amount of the contributions available for release.”

The spokesperson also noted that the ATO’s website and application forms “contain several warnings” for individuals using the FHSS.

“This includes advising them to check the accuracy of any pre-filled data in the determination form, and to amend it if there are errors or omissions. They are also required to declare that the information in the form is true and correct before they submit the form,” they said.

Any potential errors can be amended prior to funds being paid out. First home buyers “are able to amend or cancel their release request as long as they haven’t been paid any amounts. If they are able to cancel their release request at this point, they are then able to request a new determination to correct any errors but only if settlement on their intended property purchase has not yet occurred.

“Where an individual has made an error but has already been paid an amount through the FHSS scheme, the legislation provides no mechanism for the ATO to correct the individuals’ release,” the ATO spokesperson said.

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