Skating through the city, in a group

Urban skating is one of the few things that clearly improve with numbers: a group is visible, holds a lane and rides a good deal calmer than one person among traffic. Night rides have worked for decades for exactly that reason.

What gets checked before a ride

Knowing how to stop is the level
Here level isn't speed, it's control: one long descent splits a group in two within thirty seconds. The route says more about the level needed than any label does.
The route, and whether it has hills
A flat run along the river and a loop with climbing through the city have nothing to do with each other. It's said beforehand, because it decides whether someone should come.