As an ex Capetownian I remember the Barleycorn name. It looks like times and fashions are changing, so the social media and internet era is taking people away from live social gatherings.
You're correct that Monday is not going to work well, Sunday is much better. The venue is important. Advertising is crucial.
New acts should get 2 songs as you suggest, to test the waters.
The old guard sometimes need to get new people with new insights in.
Wishing you all the best.