Housing Expert: Do Not Buy A Home Until You’ve Watched This! | Jason Oppenheim

While certain big cities in Democratic states such as Los Angeles and New York have struggled, more moderate or "red" cities like Miami, Austin, and Las Vegas have fared better. This, Jason argues, is largely due to different local governance and policies rather than inherent geographic or demographic factors. He stresses that high taxation and crime policies negatively impact housing demand and market vibrancy, while locations with more business-friendly environments continue to attract residents and investors.

The Impact of Local Policies on Housing Markets

Policies, according to Jason, play a pivotal role in shaping real estate outcomes. He points to Los Angeles as a prime example of where overly restrictive and punitive measures have dampened economic growth, housing supply, and overall livability. Examples cited include draconian COVID restrictions and policies around homelessness, which have exacerbated the city's problems rather than resolving them. He attributes the decline in desirability and investment to a lack of pushback against poorly conceived policies, which often go unchallenged due to political monopolies in these urban centers.

The "mansion tax" in Los Angeles is a case in point. Introduced to raise revenue by taxing high-value home sales, it has instead led to a disastrous decline in luxury property transactions, reducing property tax revenue overall. UCLA's studies show the tax raised only a fraction of projected income, while sales above $5 million dropped by approximately 70%. This generated economic distortions, driving wealthy buyers away rather than resolving funding issues for homelessness or other public services.

Homelessness and Crime in Los Angeles

The homelessness crisis in Los Angeles, Jason notes, has intensified despite considerable spending—over $24 billion in eight years. Far from improving, homelessness and crime surged especially around 2022-2023, exacerbated by lax enforcement, bail reform, and policies that have inadvertently discouraged policing. He points out that physical security and law enforcement staffing levels are at historic lows, contributing to increased property crime and personal safety concerns that directly impact real estate desirability.

Los Angeles' policies, such as eliminating cash bail and promoting early release of inmates, have allowed repeat offenders to circulate freely, eroding community safety. Jason personalizes the issue by sharing his own experience with break-ins and neighborhood decline. He acknowledges some recent improvements but remains skeptical until the underlying policy infrastructure changes significantly.

The Realities of Housing Affordability and Supply

Challenging widespread media narratives, Jason disputes the idea of a housing shortage or affordability crisis. He explains that America, and Los Angeles specifically, have more housing units per capita than ever before, partly due to population decline as many residents have left the state. He also highlights the historical correlation between median wages and rental rates, showing rents have largely tracked wage inflation consistently over several decades.

Interest rates play a crucial role in perceived housing affordability, but even accounting for recent rate hikes, Jason argues that renting remains a viable alternative for many. He emphasizes that affordability discussions often conflate buying power (which depends on mortgage rates) with actual housing costs (represented more accurately by rent). Therefore, he calls for a more nuanced approach in assessing affordability rather than relying on alarmist soundbites.

Rent Control

Jason takes a critical stance toward rent control, explaining that while it can provide short-term relief to tenants, it ultimately reduces supply and investment in housing, driving up rents over the long term. He discusses how landlords and developers in cities like Los Angeles are discouraged from building or maintaining multi-family properties due to these regulations, further worsening market conditions.

He also touches on the unintended social consequences of rent control, such as buildings that lose value, disincentivize upgrades, and encourage owners to keep properties vacant or convert them into luxury housing. The resulting shrinking housing stock paradoxically worsens affordability, especially for the population rent control policies are meant to serve.

Legal Landscape Affecting Landlords and Tenants

California's legal environment around landlord-tenant relations is portrayed as increasingly hostile and complex, with numerous laws heavily favoring tenants, often to the detriment of property owners. Jason highlights how laws have made it almost impossible for landlords to evict tenants, even in luxury homes, unless landlords themselves move back in for a minimum of two years. Security deposit limits, anti-discrimination rules that bar criminal history screening, and new ordinances requiring clear postings about tenants' rights contribute to a legal minefield.

He details schemes where tenants leverage minor habitability claims—like mold or insects—to force expensive settlements, sometimes leading to mass lawsuits that can financially cripple landlords. This, coupled with provisions that protect tenants under "protected classes" regardless of employment status or potential misconduct, creates an environment ripe for abuse and legal harassment, which in turn deters investment in residential rental housing.

Investment Strategies for 2025 and 2026

When asked about his personal investing philosophy for the near future, Jason shares a strong preference for low-risk government bonds, specifically 30-year Treasury bills, including leveraged ETFs that multiply yield exposure. He justifies this by pointing to current treasury yields of around 5%, which offer guaranteed returns with minimal risk, while projecting that interest rates will likely decline, increasing bond values further.

Jason also maintains investments in the stock market but advises caution with real estate purchases, especially in markets inflated or mismanaged by policy. For new buyers or investors, he recommends renting over buying in many cases until market conditions stabilize or "clean up." Multifamily properties in Los Angeles and San Francisco present opportunities for more risk-tolerant investors due to their depressed prices, though he personally finds dealing with tenants and legal risks unappealing at this stage.

AI, Technology, and Macroeconomics

Jason acknowledges the transformative impact of AI and automation, predicting deflationary pressures that could further influence Fed policy towards lowering interest rates. With increased efficiency and job displacement expected in coming years, the economy will face shifts in employment and consumption that might reduce inflationary pressures, benefiting bond and stock markets.

He stresses the importance of taking a macro perspective rather than getting bogged down in technical minutiae, advocating a straightforward approach to investing based on broad economic trends rather than market noise. His confidence in impending rate reductions underpins much of his bond investment strategy.

Real Estate Market Nuances

The geography of investing remains key in Jason's analysis. He advises against buying in overbuilt or rapidly expanding markets like Austin, Miami, or Las Vegas, where there is virtually unlimited land for new construction, putting downward pressure on prices. Conversely, cities like Newport Beach, where land supply is extremely limited, tend to hold and increase in value even in tougher markets.

Jason suggests investors focus on properties with constrained supply and inherent scarcity to maximize long-term appreciation potential. This fundamental principle underlies his cautious approach to buying in markets where rapid expansion and weak zoning laws dilute value.

Personal Philosophy on Money

Throughout the conversation, Jason touches on his personal evolution in managing stress, negotiation, and money. He has moved away from micromanaging or "nickel-and-diming" contractors, valuing peace of mind and quality of life over saving small amounts of money. His spending habits reflect an abundance mentality, purposefully using money to reduce stress and increase happiness through experiences, convenience, and generosity to friends.

He emphasizes the benefits of being relaxed in negotiations and trusting professionals, sharing the philosophy that money is meant to be used for enjoyment and not hoarded unnecessarily. This approach extends to his business management style, where he aims to cultivate a positive work environment through encouragement rather than harsh criticism.

Mental Health, Therapy, and Personal Growth

Jason reveals a significant personal journey from a high-stress, reactive mindset to a calmer, more thoughtful disposition facilitated by therapy and self-reflection over several years. He credits therapy with helping him develop emotional regulation, reduce unnecessary anxiety, and improve interpersonal relationships, including those with his brother and employees.

He advocates for mental health care as vital to professional and personal success, viewing self-improvement as an ongoing "gym for the mind." Jason also foresees AI playing an increasingly important role in delivering therapeutic support, potentially surpassing human therapists by synthesizing large amounts of personalized data.