Hey there.
I see you are trying to nip the early wakings in the bud with a super late bedtime, but I think that's made him overtired and making napping difficult. I say this from experience lol - I too thought I late bedtime was the way to fix the early waking, and while it may work - most often it breaks something else in the routine.
I can't see how long your catnap is - but assuming its the average catnap length of 30m, 530pm til 9pm and a really long time for him to be awake before bedtime - especially if he does less then 2h awake times the rest of the day, know what I mean? In my opinion 8pm is even too late of a bedtime, and really. At this age you want to offer an 11.5-12h night. An overtired baby will wake early because they are unsettled. The DF being so close to when he went to bed, also may be making things rough.
I just wanted to mention that sometimes its better to BF/bottle then offer solids, as Breastmilk or formula should be what baby fills up on, not solids until after 12m. You may want to flip around the way you feed, to ensure that hunger isn't an issue - just a suggestion to take or leave naturally. You do what works best for your baby.
When we add A time, doing it in 5m increments every 2-3days is sometimes best, stopping if baby seems to be getting overtired from the switch. I sugget something like this to be your goal, after moving things slowly:
7am wake BF/bottle
8am Soilds
915am Nap 1.5h
11am BF/bottle
12pm Solids
1pm Nap 2h
3pm BF/bottle
4pm Solids
515pm Catnap 30m
630pm BF/bottle
Bath, top off if you do that, wind down
715/730pm Bedtime
DF 10-11pm
Of course this is a suggestion only, always watch your baby. Moving all of your times slowly will be key.
In the meantime - if you get a short nap, yes put him down earlier for his next nap to help lessen the overtiredness. You can always attempt to extend a short nap, but in my opinion having it work past 3m is rare. You might be better just getting him up and watching for cues to put him down again. You know him, if you think he is going to go back to sleep, by all means try. The key I think will be to offer as much sleep as you can - he needs to catch up on his sleep from a late bedtime, early wakings and now short naps. I would pull the bedtime back as soon as you can.
As he catches up and things smooth out, see how the A times are. He may in fact need more A time after he isn't overtired. Again, move slowly and watch him as you go. Any changes you make in the routine... after you make them and are where you want to be, sometimes it can take a week or more to see the results of the changes you made.
I hope something here is helpful. Congrats on propless sleep, that is fantastic! Let me know how I can help.
Zoey