Our CCRs specify that dues are due monthly, and originally that's how most homeowners paid them. Since we have always been self managed and the books are maintained by the treasurer, that was a lot of work. About a dozen years ago or so, in the dues notices, the board started requesting homeowners pay annually if possible, bi-annually or quarterly if not. The carrot was that all of the work was being done by the volunteer board, and we wouldn't need to take on the expense of a management company if people would pay quarterly or annually. Beyond that, many people would just rather write checks less frequently. We didn't change the CCRs, so technically members can still pay monthly, but at this point, only one out of 65 homes does. Even they have said they would prefer to pay quarterly, but with two young ones, their finances are tight. I'm happy as long as they keep paying
One thing that helps is that our dues are relatively low, currently $530/year. If they were $200/month, I'm sure more people would want to pay monthly. You mention billing, we don't send bills per se. We post a notice on the community sign board by the exit gate and send reminder emails. The emails include the quarterly, bi-annual, and annual amounts (as appropriate for the given quarter) and don't mention a monthly amount. If members ask about monthly, we do give the the monthly amount. We have a master email list with all addresses, and then create subset mailing lists for the quarterly and bi-annual members so the annual payers don't get the quarterly and bi-annual emails and the biannual members don't get the quarterly.
Escaped former treasurer and director of a self managed association.