DD is 8.5 mo too. Our case is pretty much like yours. We always had some problems for naps, but generally she slept all night since she is 4 mo.
Last month, she started to wake up 2-3 times at night, crying. She started to wake up early too, sometimes as early as 4.00.
So, I have modified the routine a little bit. She used to take 3 naps (45 min am nap at 9.00-9.30, 1.5 h pm nap at 1.00, and catnap at 5.00 - she also started to extend the catnap to 1.5 h). I have decided that it was time to move to 2 naps.
I am trying to extend the am nap to 1.5h, still no success(the am nap is back to 9.00). I moved the pm nap to 2.00 so that she wouldn't be overtired until the bed time around 7.30.
She is still waking up 2 times, but goes back to sleep easily with just 5 seconds of shh. The early waking problem is solved so I think that I am on the right track.
I have noticed that DD is getting tired earlier in the mornings. The routine is going better since I put her down for the nap at 9.00 instead of 9.30 or 10.00. Maybe it will work for you too.
Have you tried to sing to your LO when he is awake? Generally it works better than PU.PD for us for the night wakings. When she hears my voice, she starts to self-soothe and goes to sleep. But when I show up for PU.PD, the crying goes worst the moment she sees me.
Please keep posting the results