As I understand it, running elections is labor intensive. There was/is a plan in the works to make them less so, enabling multiple sites to run elections simultaneously. Example -- (comment by @Catija): "one of the things that's supposed to happen this year is an automated elections process that will make it much easier for us to run many elections simultaneously."
However, @Catija recently wrote
Shog was the one building the new election system so I don’t know what we’re doing right now though I’ve been told it’s a priority. For most things that require changing site settings, it’s a matter of a few factors - whether we customize it, if there’s a demonstrated need, if we have time to review requests. A great many things are possible.
Dear Stack Exchange,
Can you give the community an approximate idea of the target date range for small sites' moderator elections? Is it safe to say there will be no small site elections in February? Are they unlikely to occur in March as well?
Will the Community Management Team be taking the initiative to run elections at Writing, which currently has zero active moderators?
In the case of small sites that have only one or two moderators, will it be up to the existing moderator(s) to request an election?