Achieving Quorum. Association elections are different from municipal elections in that HOAs must meet quorum requirements and cities don't. For example, in the May 2013 mayoral election in Los Angeles, only 19% of eligible voters cast ballots. The dismal turnout did not derail the election as it would in a homeowners association since no quorum was required. If city, state and federal elections needed 50% of the population to vote before they could count ballots, elections would become impossible. Because associations are are burdened with quorum requirements which often cannot be met, boards must nag and cajole members to vote and sometimes offer incentives.
Raffles. There is nothing illegal or improper about raffling off one month's dues, gift cards, bottles of wine, a dinner at a local restaurant, etc. One month's dues can be refunded to the owner out of the general account. The mail-in ballot envelope with the person's name and address can be used as the raffle ticket for the drawing. Normally, any entity that wishes to use a raffle as a means of raising funds must register with the Office of the Attorney General. (Penal Code 320.5) However, raffles are exempt if they do not require any of the participants to pay for a chance to win. Since the raffle is being used to meet quorum requirements rather than raise money, associations do not need to register the raffle with the Attorney General's Office.
Fines. Offering incentives to vote is better than fining owners.
Amendments. Achieving quorum at membership meetings is difficult enough but reaching supermajority votes for amendments and restatements is nearly impossible. Because of that, the Legislature created the "4275 Petition" as a mechanism for realistically amending documents. If an association can obtain at least 50% membership approval, it can ask the court to approve amended or restated CC&Rs. By statute, the association must demonstrate to the court that they made extraordinary efforts to obtain voter participation. Offering $5 gift cards to voters would be one of those efforts (along with extended voting periods, repeated requests to vote, raffles, etc.).
Recommendation: To make board elections more manageable, your association should amend its bylaws to eliminate quorum requirements and cumulative voting for the election of directors. In addition, it should lower CC&R amendment requirements from a super-majority to 50%. Once that is done, future elections will be much more manageable.
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