Overstock.com Employees Weighing Oklahoma: Lower Costs, Lower Taxes, and a Different Kind of Retirement

Healthcare Provider Update: Healthcare Provider for Overstock.com Overstock.com provides its employees with health insurance options through major insurers offering Affordable Care Act (ACA) plans, including well-known providers like UnitedHealthcare and Anthem. Potential Healthcare Cost Increases in 2026 In 2026, employees at Overstock.com are expected to face significant increases in healthcare costs, driven by anticipated premium hikes in the ACA marketplace. Projections indicate that some states might see premium increases exceeding 60%, exacerbated by the potential expiration of enhanced federal premium subsidies. As many employees may bear a larger share of healthcare expenses, it is crucial for Overstock.com workers to stay informed about their benefits and explore strategies to manage rising costs. The combination of inflated medical expenses and changing employer strategies could lead to a challenging healthcare landscape, stressing the importance of proactive financial planning. Click here to learn more

'Overstock.com employees weighing a move from California to Oklahoma should recognize that differences in state taxes, property values, and cost of living can influence how long their retirement savings last.' — Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'Overstock.com employees evaluating retirement options can benefit from comparing states like California and Oklahoma, where differences in taxation and living expenses may directly impact long-term financial stability.' — Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article we will discuss:

1. How taxes in California and Oklahoma impact retirees and their income.

2. The differences in cost of living, property values, and daily expenses between the two states.

3. Programs and lifestyle considerations, such as Tulsa Remote and health care access, that may influence relocation decisions.

The thought of leaving behind California's vibrant cities, golden beaches, and Mediterranean-like climate may seem unthinkable to many residents. The state continues to draw attention from around the world because of its world-class amenities, varied cultural life, and natural beauty. However, California's growing cost of living, high state taxes, and skyrocketing housing costs have put a heavy financial burden on those on fixed incomes like Social Security and pensions. Some employees at Overstock.com are therefore looking at alternatives that offer a more sustainable retirement way of life. Oklahoma is one place that is becoming more popular.

Due to advantageous tax laws, reduced housing prices, and even incentive programs like Tulsa Remote, hundreds of Californians have moved to Oklahoma in recent years. ¹  While Oklahoma may not be the best option for every retiree, there are sufficient financial differences between the two states that they should be carefully considered.

California versus Oklahoma Tax Comparisons

Retirement planning heavily relies on taxes, and there are significant disparities between California and Oklahoma. The tax code in California is particularly difficult for retirees who have several sources of income, according to Carlos Hernandez of Wealth Enhancement. Although Social Security benefits are not taxed in California, the state's progressive tax system applies to pensions, 401k contributions, and other retirement income. Rates can reach 12.3% for many taxpayers, while the highest incomes can pay up to 13.3%, ²  which is the highest state income tax rate in the country.

In contrast, Oklahoma offers retirees 65 and older a $10,000 deduction on other types of retirement income in addition to exempting Social Security income from taxes. ³  Oklahoma's highest marginal income tax rate is 4.75%, ³  which is far lower than California's even without taking this deduction into account.

These differences can result in annual tax savings of thousands of dollars for seniors who receive both Social Security and pensions. Take, for instance, a person who receives $30,000 in Social Security benefits in addition to a $40,000 pension. The pension income would be subject to full state taxation in California. In Oklahoma, Social Security would be completely untaxed, $10,000 of the pension income would be exempt, and the remaining taxable pension amount would be subject to significantly lower rates. As a result, the tax burden is considerably lighter, giving the household budget more flexibility.

Cost of Living and Property Values

The financial equation consists of more than just taxes. The housing market in California puts additional financial strain on seniors, claims Kevin Won of Wealth Enhancement. California routinely has some of the highest property values in the country. The base property tax payment is still correlated with high market values, despite the fact that established safeguards like Proposition 13 restrict yearly increases in property tax assessments. The absolute cost is nevertheless high in comparison to national norms, even if householders 55 and older may relocate their tax base under specific circumstances. ⁴

The problem is made worse by insurance premiums. In California, plans that cover the danger of earthquakes or wildfires are not only costly, but they are also getting harder to obtain in high-risk locations.

The real estate market in Oklahoma paints a completely different picture. Compared to many California regions, the median home value is less than half. ⁵  Reduced property taxes are a direct result of lower property prices. Although Oklahoma does not provide tax-base transfers or unique senior exemptions like California does, retirees frequently still benefit from lower total valuations.

Additionally, Oklahoma benefits from a lower overall cost of living. Daily costs, such as groceries, utilities, and medical care, are often less than in California. Retirement savings can extend further thanks to the combined impact of lower housing, insurance, and daily expenses, which gives people greater flexibility in choosing their spending and lifestyle preferences.

Rewards Initiatives: Tulsa Remote

Tulsa Remote is one distinctive program contributing to Oklahoma's rising popularity. This program was started in 2018 with the goal of luring remote workers to Tulsa by providing cash incentives and opportunities for community integration. The program offers $10,000 to participants who agree to stay in Tulsa for a minimum of one year.

Over 60,000 applications have been submitted to Tulsa Remote since its launch, with almost 8,000 of those applications coming from California. ⁶  As a result, nearly 3,600 participants have relocated to Tulsa. ⁶  Despite focusing on working professionals rather than retirees, this program has helped spread awareness about Oklahoma's affordability and livability.

The Practical Financial Impact

The practical impact is better demonstrated by going over the previous financial case again. In California, a retiree with $40,000 in pension income and $30,000 in Social Security would pay high taxes; nevertheless, in Oklahoma, they would receive large benefits. Once the $10,000 exemption and reduced marginal rates are applied, the difference could result in yearly savings of thousands of dollars.

Beyond taxes, long-term financial consistency is strengthened by being able to buy a home for half as much, or less, than in many California markets. Over time, lower utility costs, lower insurance premiums, and overall cost-of-living reductions can add up to provide more discretionary income for leisure, travel, or building retirement stability.

In Conclusion

Although California is still a popular place to live, seniors are finding it increasingly difficult to keep up with the state's high taxes, high property values, and overall cost of living. Oklahoma is a strong alternative because of its low tax rates, $10,000 retirement income exemption, reasonably priced housing market, and lower cost of living.

According to a recent analysis, retirees in Oklahoma could maintain their financial resources for roughly 51 years with $1.5 million in savings and Social Security benefits, far exceeding the 24 years estimated in California. ⁷  This difference is primarily due to Oklahoma's significantly lower annual cost of living (about $29,666) ⁷  than to California's high expenses.

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Sources:

1. MSN. ' Hundreds of Californians have been paid $10,000 to relocate to Oklahoma ,' by Hannah Fry. August 15, 2025. 

2. Nerdwallet. ' California State Income Tax Rates and Brackets for 2024-2025 ,' by Sabrina Parys. June 5, 2025. 

3. SmartAsset. ' Oklahoma Retirement Tax Friendliness .' 2025.

4. California State Board of Equalization. ' Transfer of Base Year Value for Persons Age 55 and Over - Propositions 60/90 .' 2025.

5. Forbes. ' Median Home Price by State ,' by Kiah Treece. July 29, 2025. 

6. SF Gate. ' The surprising destination luring California transplants with $10,000 ,' by Tessa McLean. August 4, 2025. 

7. CNBC. ' $1.5 million is the 'magic number' for retirement savings--here's how long it lasts in every U.S. state ,' by Mike Winters. Mar. 15, 2025.