Leo sounds a little OT, hun
I wonder if a slightly earlier BT might help Leo? Just say 15min before Lewis to give him that touch more and not mess with your day too much? If Lewis is waking Leo in the morning (WDYT?), he may just need that bit more in the evening.
They're doing very well on one nap for such young fellows, really.
Ear infections are so tricky, they can be so painful and they can just not bother LO - depends on so many variables. DS doesn't even notice he has them most of the time and the doctor winces when she sees his infections. It could be that but generally when going to pen nap initially, a shorter nap with unsettled waking is OT/discomfort even though its not that typical 30 min nap. That BT a touch earlier for Leo and thus a slightly longer night may well help. So glad to see they tacked on that day when they had two short naps when you were out and about, such a great sign