Steve,
The Board is likely in violation of the terms of the covenants by waiving the assessment.
If you want to pay an Officer (which is what you are doing) for their work, you should write a check and give it to them.
If the individual doesn't want to provide you with the information required to file a 1099, then fire the individual.
NOTE: Paying the individual causes some issues for them as well. They will be considered a professional and not a volunteer. Therefore, they will not be covered by the protections of the
Federal VOLUNTEER PROTECTION ACT OF 1997.
Additionally, the Association may have inadvertently hired an employee (vs. an independent contractor) and be subject to your share of payroll taxes (which I get the impression you are already aware of). To help determine if an individual is an employee or contractor, see the following IRS web site:
Understanding Employee vs. Contractor Designation.
OH, make sure you are filing the correct 1099.
Waiving the dues means you file
1099-C (forgiveness of debt).
Paying for services (writing a check) would be
1099-MISC If the Association wants to maintain compliance with IRS rules regarding the 1099, the Association can still issue a 1099 without a SSN or EIN.
However, it must be done correctly: 1) Make a formal demand for the SSN/EIN (written request, copies kept) prior to the end of the year (i.e. do it now).
Include
IRS form W-9 2) If you do not get the SSN, file the 1099 but leave the SSN/EIN blank.
3) When the IRS contacts you (and they will) about the missing SSN/EIN, follow those instructions. Note: The instructions will instruct the Association to withhold taxes and send them to the IRS. Additionally, the individual will be subject to a $50 penalty for failure to provide the SSN to you. see:
What if a Company Refuses to Provide a W9? Perhaps, making this individual aware of this issue will have them comply.
Hope this helps,
Tim