As a homeowner, your goal is to enjoy your home while keeping costs low. Ideally, you’d convince the property assessor you live in less-than-stellar conditions to lower your property taxes, especially during a bull market where taxes tend to skyrocket.

However, when the market is booming, it’s easy to become complacent about expenses. It’s crucial to actively manage your finances and look for ways to boost your income to prepare for any potential economic downturns.

I once talked to someone from the property assessor’s office who candidly explained that they capitalize on homeowner complacency. They rarely adjust valuations down during market dips because few homeowners challenge these assessments, and they max out tax hikes when the market’s up.

This conversation was a wake-up call for me. It led me to challenge my property tax assessment by compiling a list of lower-priced homes sold nearby to justify a lower valuation for my home. During the 2007-2010 downturn, this strategy worked, and I managed to get some tax relief.

Then in 2015-2016, despite a strong market, I noticed a neighbor’s home sold for significantly less per square foot than the average. This spurred me to contest my property’s assessed value again. Proposition 13, which caps property value increases, played in my favor here. It prevents dramatic increases in property tax based on inflation rates, benefiting long-term homeowners who might see only minimal increases compared to newer purchasers.

Challenging property taxes, however, is no easy task. Navigating the city’s assessment website is deliberately challenging, filled with confusing links and buried information, which deters many from pursuing appeals. Once you find the right form and understand the process, you’re faced with a narrow window to file an appeal, further complicating matters.

Moreover, the property assessor’s office throws additional hurdles at you, like confusing free informal review processes with formal appeals that come with non-refundable fees. Despite providing clear evidence of my property being overvalued, my appeal was rejected. The assessor’s office argued that the sale across the street wasn’t a valid comparison due to differences in home features, which felt like grasping at straws.

This experience showed me how rigged the system feels—like fighting a losing battle against a “Black Hole” government entity that’s nearly impossible to overcome. It’s a frustrating realization that even with solid evidence, you might still end up on the losing side due to bureaucratic obstinacy.

For those not willing to navigate the convoluted property tax appeal process, consider real estate crowdsourcing as an alternative investment. This allows for investing in diverse real estate opportunities nationwide without the direct hassles of property management and contested assessments.

In the end, while the city may often win due to its daunting appeal process, understanding and navigating the system can provide at least a chance to fight for fair property taxation.