These are great questions - challenges faced by many, many private road associations. Thank you for posting!
In 2020, at our Annual Road Association Conference, MARA Board Member Roberta Manter spoke on member participation. You may find helpful suggestions in her handout on our Resources Page entitled, Encouraging Member Participation.Expanded Notes.pdf
Association by-laws are a good place for members to "vote in" answers to some of the questions you raise. Unless your by-laws so state, it is not necessary to fill every officer position. In Sample by-laws 2, on our Resources Page, Article 4, Elections, the four officer positions may be held by only 3 Board Members who manage the association between annual meetings.
Our association confines our elected officers to the owner/members. We believe the vested interest inherent in ownership of property along the road will foster the best possible service to the association. I believe your members, as a last resort, could offer officers a stipend by majority vote.