I vote June 14 for these reasons:
From the perspective of our smaller-city group: Weekend protests are much more doable for us in places like Eugene, Oregon. Most of our small team works weekdays and has to take time off to do any weekday events. Weekday national dates present a major strain on our already resource-strained team.
We get WAY more turnout for weekend events.
Also, picking national holidays/days of remembrance often lead to us having to compete with other local organizations to hold our events, rather than being able to team up with those other orgs on our respective events.
May Day, for example, has put us in planning conflict with a labor-union event that had already been planned on the ONE good spot to hold a protest in town. Similarly, Juneteenth would put us in a situation where we are in conflict with POC-supportive organizations for the narrative and crowd of that day, and would require us to support/combine with their events rather than hosting our own. (We want to support them too, but it complicates things when that is the day that we have to advertise our own event).
In this case, we were not able to join up with them. The labor union was only expecting a crowd of a couple hundred people and they expressed that they didn’t have the staffing to manage a larger protest. They asked us to move our event. If we had moved forward and just advertised our event at that same date/time/place, it would have been a slight to them.
It’s easier done in bigger cities, where activist groups have more people and better infrastructure. In smaller cities, you have skeleton crews with small to nonexistent safety teams, and fewer suitable places to throw events. There is such a thing as “stepping on others’ toes” here.