you could really progress whenever you want. if you're getting through fairly easily, then definitely progress. if you're really working through that last set but still want to make the earlier sets harder, progress and allow yourself a little more rest time.
are you doing your sets back to back, or are you moving through all the exercises for multiple rounds? if it's the latter (supersetting) you will probably be able to hit bigger numbers just because certain muscles will have more rest time while your working others. in other words, your arms get to rest up for the next set while you're doing squats. push ups, squats, pull ups, planks, shoulder press/htpu seems to be a good order of exercises for me.