I wonder if it might make sense given we're in a period of low engagement to try to split the contest up to encourage new people to participate, like the /r/imaginarymaps people do. Maybe it would still be just one contest each round, but there could be two 'leagues' - one for people who have ~3+ wins and one for everyone else - and then have two winners each fortnight. The Map Thread is as active as ever, so clearly there isn't a real shortage of people who want to make maps.
Alternatively, maybe there could be a split from a single winner to something like 'best in aesthetics' and 'best in timeline concept.' There are a lot of people with great pixel map/QBAM skills on the forum, and they are some of the best format to tell the story of a timeline in a single image. However, they are very rarely submitted and AFAIK one hasn't won in years just because they usually don't stack up aesthetically.