Thanks for the input, I appreciate it. After a brief discussion a few days ago with the sleep consultant i used to work with she thought my baby is ready to be on two naps using a by the clock schedule as he can now handle 3 hr waketimes. As mentioned, Previous to that he was on three naps but despite large waketimes (3 hr) the first two naps were only 1 hr-1 hr 15 min and was having night wakings and bedtime battles as of late.
I don't feel like the last four days went very well though on the clock schedule and my baby is getting overtired. I would like to go back to waketimes and try not to have a cat nap as that was causing issues. I am trying to figure out appropriate waketimes for him based on how the past few days evolved on this schedule. I just don't seem to be able to get long naps still, and i know 1 hr naps can mean UT but the waketimes are pretty appropriate for his age now. Is there hope the nap lemgth will extend as he adjusts to two naps?
I will note that early morning wakings have always been very common for him and in the past he he could often put himself back to sleep for one sleep cycle before the desired waketime of 6:30 (although the gap that he is awake is longer and longer now and the chance of him falling asleep again is smaller). I don't seem to be able to get rid of this issue regardless of the bedtime or how well the naps go
By the clock schedule
Naps at 9:30 am and 2 pm.
Bedtime 6:30-7
Day 1
W 6:30
S 9:30 until 10:26 (~56 min).
S 2:00 until 2:37. Asleep again at 3:07 until 3:55. (Total = 1 hr 23 min.) (waketime 3.5 hr).
6:50 - bedtime, asleep at 7:16 (3.25 hr waketime)
Day 2
W 5:45
S 9:22 until 10:25 (~1 hr 3 min).
S 2:02 until 3:17 (1 hr 15 min) (waketime just over 3.5 hr)
6:25 - bedtime, asleep at 6:32 (3.25 hr waketime).
Day 3
W 5:36
S 9:19 until 10:21 (~1 hr 2 min).
S 1:57 until 2:53 (56 min) (waketime just over 3.5 hr)
6:25 - bedtime, asleep at 6:30 (3.5 hr waketime, very cranky at bedtime). 4:30 - wake up, asleep at 6:10.
Day 4
W 6:47
S 9:29 until 10:20 (~50 min). Fell asleep again at 10:50 until 11:31 (40 min). Total = ~1 hr 30 min.
S 2:17 until 2:49 (32 min). (2.75 hr waketime - undertired nap but had to stick to schedule)
5:40 - bedtime (did not want him to wait until 6:30 bedtime), active crying (overtired), asleep at 6:10

. Wake up at 5:30 am, asleep at 6:30 am.
Day 5 (today)
W 7:10
S?
What would be the best approach for waketimes to try to increase the nap length? I would like to try not to nap him before 9:15 for first nap but given the early risings that waketime can become very long. I am also worried that if the naps do not lengthen soon i will be stuck with early bedtimes and possibly even earlier mornings. I would love to have a more consistent routine but it is so hard to get there given the random wake up times!
Thanks so much