Ideas for Running Election Day/ COMPLICATED

I don't know if it's that complicated - your main problem may be in getting enough people to participate in the election. Begin by checking your documents - I'm sure it would be OK to have the elections held in one day.

It's important that you keep the process relatively simple For example, the ballot could be tailored so that they only list people running for a specific association and the ones running for an at-large spot. Personally I prefer that candidates make up their mind and only run for an at large spot vs. sub-association spot. If you want to allow that, I would give the sub-association election higher priority - if you win that, you're dropped from the at large race, or the next highest vote getter in the at-large election will take that spot

People can either send in a ballot, appoint a proxy or come to the meeting. At the meeting they can sign in on a list showing their association and then receive the appropriate ballot. For those who sent in a ballot, you can set up a separate list, so you know those folks won't vote again. Of course, if they change their mind, you may have to find their ballot and destroy it before giving them another.

But mostly, you need to educate people on the importance of the election and encourage them to either mail in a ballot or appoint a proxy to vote for them at the meeting. Be sure people receive information on all candidates, perhaps holding a meet the candidate meeting where everyone can ask questions - separate meetings on the same night for each sub-association could work so issues specific to their community could be discussed.

Having this occur successfully would require quorum from all sub assns as well as the cumulative master assn which would require lots of campaigning/reminders from whoever is running the process to ensure that quorum is achieved for all.

But suggest a single ballot be created that has 2 sections: a master assn vote and a sub assn vote.

Sub assn voting section would list each sub assn and their candidates and require voters to find their listed assn and vote for only one individual to serve as their sub assn board member. Highest vote getter wins that seat for each sub assn.

The master assn section would have a compiled listing of all candidates from all sub assns. and voters would select two names (for the two positions). Highest and second-highest vote getter would win the two seats. If either of those two were already selected as a sub assn. board member, then the next highest vote getter would get the position.

A well-written ballot, absentee ballot, and proxy with simple, brief instruction would go a long way to helping folks understand and hopefully fill it out correctly the first time.

Not sure about FL voting requirements, but if electronic voting means are allowed, perhaps look into that as a way to try and achieve quorum.