Murph, thanks for checking out our game!
Gangs – In the Regiment, force parity rules replace the gang rules from Apocalypse World. It’s not really explained in the play test kit what exactly overwhelmed or onslaught means; but, for now let the subjective descriptors serve as a guide.
While the PCs may make moves that affect or involve NPCs, the PCs don’t actually make rolls on their behalf of NPCs. So, unlike AW, you don’t roll for your gang. The squad or team are influenced by the PC’s actions, particularly if a PC is in charge; but, in the Regiment, what the NPC soldiers do and how they perform are entirely in the hands of the GM.
NPCs and gear – in the fiction, the NPCs are clearly carrying their own equipment. In game mechanics terms, the “gear” they carry isn’t tracked, that’s a level of detail we don’t want the GM to have to track or think about. So, the GM decides if the NPCs have adequate gear to do what they ought to be doing. The GM can use the unit reserve, in particular, as a guide to gauging the gear state of NPCs. Also, move successes or failures. In general, the NPCs are assumed to have what they need to get the job done unless the GM decides it fits better with the fiction to use surplus or shortage as a thing.
Repeating moves – I think it’s contextual whether repeat moves are the right approach. So, no hard and fast guidance there. In making any move, there has to be a means or opportunity in the fiction to do so. In the Regiment, harm can be a hard move; but, it’s also a fact of the circumstances, so you didn’t have to “spend your hard move” to deal harm. In fact, the GM makes whatever hard moves are appropriate. That said, the question should be, what was the tactical significance of the PC’s failure to make the close assault? Is their team shot to pieces (call for the when you see a fellow soldier go down in battle move)? Do the enemy secure their position and suppress the PCs (give them a condition – make them endure fire, push for rally)? Do the enemy press their advantage and attempt to overwhelm the PCs (hold fast under fire)? What the enemy do and how the PCs attempt to make the move should determine whether or not it makes sense to follow up one failed move with the same move.
Standard training – You have the right perspective. There is a fine line; but, there’s an art to storytelling ;)