Is this a male

You can do either or. I would say the easiest would be to let nature do it's thing and just keep them all in the room together. But also you could shake the male over the females Or you could choose specific spots on the females and place the pollen carefully so that you still have usable buds with your harvest as well as seeds. Best of luck, I'll be starting my own breeding project soon as well

Unfortunately, the last picture looks like pollen sacs are forming.

If you have them all in one tent, you can just let the fans blow the pollen around, it will pollinate on its own, no need for the paintbrush. Keep in mind, it will produce a ton of pollen. You will need to thoroughly clean everything after the grow or you’ll have seedy buds for a while. If you have these in separate tents collect the pollen and paint it on. Saves the big clean-up afterwards.