In Massachusetts, condo owner joins HOA board, then finds suspicious checks linked to one woman's bills

A Massachusetts condo owner said joining the HOA board revealed what looked like years of questionable spending in a self-managed 20-unit HOA.

The owner alleged that one woman had been writing association checks for "bills that are clearly her own" and taking "several hundred dollars each month for years."

Here's what to know

According to the Reddit thread, the Massachusetts buyer first became concerned after seeing what they viewed as financial "red flags" in the 20-unit condo association. They said the board ignored requests for records, so they sought a board seat. After getting elected, their review found "suspicious financial activity" and that the HOA had "literally no documentation on anything."

By that point, the poster said neighbors wanted to move forward with a "fresh start," believing they had already "stopped the bleed." They also wrote that the woman who had long overseen the finances "refuses to acknowledge any of the charges."

Several replies steered the discussion toward insurance rather than a direct courtroom fight. One commenter said Massachusetts requires condo associations with more than 10 units to carry crime or fidelity coverage, adding, "So in theory, your insurance policy should handle it (and then they can pursue her on their own)."

Another commenter urged the board to document its choices carefully, writing, "You can't forgive money that isn't yours." 

The dispute centered on whether pursuing repayment would protect owners or instead create a long and expensive fight.

More background

Across the country, homeowners have also faced associations that block money-saving property upgrades, including rooftop solar panels and native plant lawns, turning private rules into a real financial issue for residents.

Because condo owners share common finances, questionable spending can impact the whole building. The poster said this was not the first time the issue had surfaced: a former board member had tried to press it, but neighbors "voted 'No' on an audit" since the woman at the center of the dispute had known everyone for years.

Commenters noted that proving fraud becomes harder when records are missing. 

One user wrote, "Police, prosecutors, and even yourself can only act on what can be proven," while another said, "This sounds like straight up fraud."

In a 20-unit building, money siphoned off over multiple years could leave owners absorbing the loss through higher dues, deferred maintenance, or special assessments.

What can be done?

Commenters repeatedly pointed to the HOA's insurance policy as the most straightforward place to start, specifically asking whether it includes employee dishonesty, fidelity, or crime coverage. Their view was that, if the policy does, the board could assemble whatever proof it has and submit a claim instead of trying to chase repayment by itself.

Just as important, some replies emphasized creating a record of every decision. Suggestions included recording the board's concerns and the owners' response in the minutes, then holding a board vote on any insurance claim and documenting that action in writing.

The original poster also said they already have a lawyer, though the attorney reportedly told them the choice to keep pushing is ultimately theirs.

Where can I learn more?

Other homeowners have described HOA disputes over charges, billing, and questionable decisions.

• A condo owner was stunned by hidden fees and unusual billing tied to submetered utilities.

• Families pushed for an investigation into HOA charges over amenities their neighborhood never had.

• In Las Vegas, a homeowner fought a sudden $15,000 bill after HOA claims of damage.

• Across several communities, HOA horror stories caused uproar over vegetation disputes, fines, and enforcement.

• One homeowner faced a bizarre HOA demand after years without issues.

Get TCD's free newsletters for easy tips, smart advice, and a chance to earn $5,000 toward home upgrades. To see more stories like this one, change your Google preferences here.