Thanks Zoe and thank you so much Sara for taking the time to try to brainstorm an idea that might work! And to do so when you're in the midst of some pretty awful stuff with your boys so sick! So thank you!

I've been pondering your idea all afternoon/evening. At first I was ready to jump on it and give it a try but the more I thought about it the more I wasn't sure it would work. I don't want to be a nay-sayer or shoot the idea down. I've really given it a lot of thought, but these are a couple concerns I have:
1) As far as I know from the past, Aaron won't go to sleep UT. He'll just roll around and work himself into a state of OTness. While he would've gone to sleep after 4 hr A today I think that's because he was still recovering from his horrible night on Thursday. I think most days he won't go down after 4 hrs A. As well, the idea of trying to figure out what A times that will result in 2 45 min naps truthfully overwhelms me. I think it would take weeks to figure out something that would work (if that would even do it) and unfortunately in the past no matter when or how long Aaron's morning nap was (even when it was capped at 30 min), he only slept 30 min in the pm and would scream when I'd PD for that nap. I don't know if I have it in me to go through that again.

2) 2 times a week I have a mom's group at 10:00 so there's really no way for him to have an am nap on those days and I really don't want to quit that as I think it's really important. I do want Aaron's sleep to be better but I'd have to stop going to that group if we go back to two naps.
3) Aaron starts at the home daycare soon and it is going to be a gong show. He will not sleep anywhere else so we know he's going to scream and scream when she tries to put him down for the nap at her house. I think I'd rather put her (and the other daycare kids) through only one nap screaming fest a day than two.
For those reasons I think I'd honestly rather suffer through the NWs and broken sleep and stick with the current plan, even though it isn't working very well. Are my concerns reasonable? Or do you think I should still consider trying two shorter naps?
The only other options I thought of were:
1) move set nap earlier as I've been getting the best naps when he wakes up between 7/7:30 so an A time of 5-5.5 hrs. Since WU goal is 6:30 (I have to get him up at 6:30 on days that I work) perhaps I should move the nap to 12:00?
2) move BT 30 min earlier to 6:30 to give him more opportunity to tack on at night even though he's not very reliable with this