Transparency Denied
The Board President Put It In Writing
February 14, 2026
On Feb 10, 2026, 175 E Delaware Pl HOA Board President Scott Timmerman, replied to my Holiday Fund records request with an email intended to end the conversation. Instead, it confirmed that the Association provides confidential employee data to the committee, that no 1099s were filed, that the Fund has no legal structure, and that employee payouts can be reduced based on subjective judgments with no written policy. Every answer created a bigger problem than the question it was meant to close.
Brought to you by Drew McManus, your neighbor in 7908.
What The Board President Confirmed
After weeks of silence and a three-page denial from the HOA’s attorney, Board President Scott Timmerman sent a response on Feb 10, 2026. It seems he intended to shut this down. Here’s what he put on the record instead.
- The Association provides confidential employee data to the committee, including years of service and whether the employee “was on duty throughout the year.” The HOA’s attorney said the Fund is independent. The Board President just confirmed the Association feeds it personnel information.
- The Board President personally selects who runs the committee. He describes this as recognizing “volunteer services,” but the mechanism is the same: the Association’s top officer picks the leadership.
- No 1099s were filed. Timmerman claims the Fund acts as an “agent” for contributing owners, not as a business, so no tax filings are required. That’s a specific legal position with substantial consequences if the IRS disagrees.
- The Fund has no legal structure. No incorporation. No trust. No entity of any kind. Two volunteers personally hold and distribute over $100,000 with no legal structure around them.
- The Fund is not registered with the Illinois Attorney General. Timmerman says the contributions aren’t charitable. The Illinois Solicitation for Charity Act may define that differently.
Scott Timmerman, Feb 10, 2026
Drew,
The HOA has a policy where all Document Requests are sent to our Attorney for review. Accordingly, it appears that you were already informed that the Association does not control the Holiday Fund and is under no obligation to respond. However, I will provide the following information.
As you are already well aware, the Holiday Fund is a voluntary pool of money collected from participating residents and unit owners which is distributed to building staff members. Participants’ voluntary contributions to the Holiday Fund are deposited into a segregated checking account controlled by two trusted volunteer unit owners, who are signatories on that account and act as agents for all contributors to the Holiday Fund. Because the Association’s Board of Directors has not been authorized to – and cannot – direct the distribution of private contributions to the Holiday Fund, the Holiday Fund is not under the Association’s control. For 2025 Holiday Fund distributions, the trusted volunteers who served as chairs of the Holiday Fund committee were Nike Whitcomb and Alicia Williams, both of whom have worked on and run the fund in the past. The Board does not vote or provide direction on any actions taken by the trusted owners and the committee who administer the Holiday Fund. The members of the Holiday Fund committee are unit owners who volunteer to serve in that capacity and are selected by the committee chair. The selection of the chair by the Association’s President was based on them faithfully providing volunteer services in the past.
Lest it go unsaid, no one is obligated to contribute to the Holiday Fund, and if you have any concerns whatsoever about the Holiday Fund or how contributions are distributed, you need not participate. Indeed, any owner wishing to tip our HOA employees is more than welcome to do so on their own. However, this is logistically difficult for any owner wishing to tip all employees because they would need to identify, locate, and hand a tip (check/cash) to each of our 32 workers. There are numerous staff behind the scenes who tend not to be visible to residents. The Holiday Fund provides a convenient way for owners to provide tips to every employee in recognition of their hard work throughout the year.
The trusted owners who administer the Holiday Fund are not, and do not need to be, organized or incorporated as a separate legal entity. The Holiday Fund does not engage in any trade or business and does not receive any interest income or other taxable income. Therefore, it does not file income tax returns. 1099s are issued by entities that are engaged in a trade or a business. Just as unit owners who make a holiday gift to a staff member do not issue a 1099, the Holiday Fund acting as the agent for those contributing owners does not issue 1099s to staff members who receive distributions. Each staff member is responsible for reporting and paying any taxes due on Holiday Fund distributions. The Holiday Fund is not registered with the Illinois Attorney General as a charitable organization, as the funds it collects are not charitable contributions. The members of the Holiday Fund committee are volunteers who devote their time and energy in the interest of the building and its residents. In the event of a theft of Holiday Fund monies, the wrongdoer would be exposed to liability from those who contributed to the Holiday Fund.
Retention of personnel is important to the Association, and facilitating distribution of the communications by which owners and residents are encouraged to provide holiday season gifts to staff is very much in the best interests of the Association. The Association provides the Holiday Fund committee with information on each staff member’s years of service and whether the employee was on duty throughout the year. Staff members who were on duty throughout the year and have more than 5 years of service receive the same distribution amount. There is a graduated reduction for staff serving less than 5 years. Adjustments may be made to the distributions for staff members who were not on duty throughout the year.
Scott Timmerman
TimmermanHOA@gmail.com
The “$400” Problem
The HOA’s attorney told me the Association’s resource contribution to the Fund was “estimated at no less than $400.” During my document inspection on Feb 11, 2026, the Association produced two invoices from Chicago Print Plus totaling $2,681 for printing, folding, stuffing, postage, and mailing labels; all billed to Sudler Property Management, the building’s management company.
- 1,000 employee Holiday Fund envelopes: $395 (invoice)
- Production of 610 Holiday Fund letters, folded, stuffed, with postage and mailing labels: $2,286 (invoice)
- Total: $2,681
These costs covered the flyers distributed under resident doors as well as the formal mailings sent to owners, which included return envelopes with prepaid postage for submitting paper checks.
Both invoices were billed to Sudler Property Management, the building’s management company. Not to the Holiday Fund. Not to a separate entity. Not to either Holiday Fund Committee co-chair Williams or Whitcomb.
When I asked who authorizes the under-door distribution of Holiday Fund materials, the Community Association Manager responded that “the Holiday Fund Committee requests distribution.”
The question about authorization was answered with “requests.” Do you think an independent organization of the type Timmerman described can submit requests to an HOA’s management company and simply expect building employees to carry them out on the clock?
When I asked about the cost of staff time spent distributing under-door flyers, I was told “we do not know how much time it takes to distribute the notices.”
The HOA’s attorney said $400. The receipts say $2,681. The staff time is unknown. And the Association can’t even describe its own role without using language that contradicts the independence claim.
Community Association Manager, Feb 10, 2026
Hello Drew,
To respond to your additional inquiries from this morning, please note that we do not know how much time it takes to distribute the notices, and I have confirmed that the Holiday Fund Committee requests distribution of correspondences related to the Holiday Fund.
Why This Is Bad For HOA Employees
Timmerman confirmed that “adjustments may be made to the distributions for staff members who were not on duty throughout the year.” No formula. No written policy. No documentation. Just “adjustments may be made.”
Let’s extend some empathy and look at this from the employee’s perspective:
- You do your job.
- You get hurt, sometimes on the job, or get sick and take the leave you’re entitled to.
- When the holiday fund checks come out, yours is smaller.
- Nobody tells you why. Nobody shows you the math.
- A group of members on a board committee decided you deserved less, and that was that.
- There is no appeals process. There is no documentation. There is no way to know in advance how your payout will be affected.
Timmerman says retention is important to the Association.
Do you think these actions align with that sentiment? How does a system that punishes employees for using approved leave help with retention?
Why This Creates Legal Risk To An Association
It seems like Timmerman’s letter was intended to end the conversation. Instead, it put the Association’s legal exposure in writing.
- The “agent” theory backfires. It seems like calling the committee an “agent” for contributing owners is meant to make the arrangement sound more official. But under agency law, every contributing owner would be a principal with a right to an accounting. Contributing owners have requested one and been denied. Timmerman’s own theory supports why any contributing owner request should be honored.
- The 1099 position is aggressive. When 32 employees receive structured, tenure-based payments from a pooled fund administered by a committee, the IRS may not see that as individual gift-giving. It may see it as organizational compensation that should have been reported.
- The subjective payouts create liability. Reducing employee payments based on approved, guaranteed leave with no written policy creates different classes of employees.
- The costs keep adding up. The HOA’s attorney said the resource contribution was $400. The actual documents show $2,681 and counting. We know there’s undocumented value for time spent administering holiday Fund activity by staff, so every dollar the Association spends defending these positions comes out of owner assessments.
What’s Next
The ten questions from my Feb 3, 2026 response to the HOA’s attorney remain unanswered. Timmerman’s email intended to address some of them. What does it tell you when the answers are more damaging than the silence?
On Feb 11, 2026, I replied to Timmerman’s email with follow-up questions about who authorized the $2,681 in Association spending, who approved sharing sensitive employee data with what the Association calls an independent entity, and how collecting $102,000 into a segregated bank account with a tenure-based formula qualifies as the same thing as handing someone a cash tip.
I also asked a simple question: the Board has the opportunity to replace this structure with an official program that operates transparently and eliminates the legal exposure entirely. What’s preventing them from making that happen?
As of the time this article was written, there has been no response. What should owners expect from a Board that keeps answering questions by creating bigger problems?
Drew McManus, Feb 11, 2026
Good morning Scott,
Thank you for your response. I appreciate you taking the time to address some of the questions I raised with Mr. Stevens.
Your letter confirms the following:
- The Association provides employee tenure and duty status information to the committee
- The Fund has no legal entity structure
- The co-chairs are Board members selected by you based on what you described as their “faithfully providing volunteer services in the past”
- The committee members “are unit owners who volunteer to serve in that capacity and are selected by the committee chair”
The document inspection also confirmed the Association spent $2,681 on printing, folding, stuffing, and mailing for the 2025 cycle.
Your letter states the Board “has not been authorized to – and cannot – direct the distribution of private contributions,” and concludes from this that the Fund is not under the Association’s control. This defines control narrowly as the ability to direct distributions. The Association selects who runs the Fund, provides the infrastructure to operate it, spent no less than $2,681 this year on its communications and operations, and supplies the employee data necessary to calculate payouts.
- What definition of “control” excludes all of these activities?
On the subject of Association resources:
- Who authorized Sudler to schedule and implement under-door distributions for the Holiday Fund using Association employees?
- Who authorized spending no less than $2,681 in Association funds on Holiday Fund printing, stuffing, and mailing rather than drawing those costs from the funds raised?
Your letter states the Fund does not issue 1099s because it acts as “agent” for contributing owners, comparing it to an owner handing a cash tip to an employee.
- How does collecting $102,000 into a segregated bank account with designated signatories, applying a tenure-based formula, and making adjustments for employees not on duty throughout the year with knowledge of and consideration of the reasons why they were not on duty constitutes the same activity as an individual owner handing cash to an employee?
Your letter also confirms the Association provides employee tenure and duty status to the committee.
- If the Fund is a separate entity not controlled by the Association, were employees notified their information would be shared?
- Who authorized that disclosure?
A Path Forward
The current structure exposes the Association to potential liability on multiple fronts: the IRS may not share your interpretation of the “agent” theory regarding 1099 obligations; the Illinois Attorney General may conclude that soliciting $102,000 annually for a stated benevolent purpose requires charitable registration; and employees whose tenure and leave data was shared with what the Association characterizes as an independent entity may have privacy claims.
If you intend to continue using this same process for the 2026 holiday cycle should you remain in the position of HOA President, please explain how the Association plans to address these concerns given that your role seems to have exclusive control over how this board activity is structured.
Alternatively, the Board has the opportunity to replace this structure with an official program that operates transparently, applies equitably, and eliminates the legal exposure entirely. What’s preventing you from making this happen?
I remain interested in resolving this matter and request answers to the questions above.
Please include this correspondence in the board packet for the February 16 owners forum.
Blue skies,
Drew McManus
Unit 7908
