Hi Sue & welcome
There are a couple of issues here.
I think the most important one is the feeding to sleep association. Are you looking to wean altogether or just the night feeds?
I also think he is quiet overtired. If he wakes at 8.30am, the nap should really be about 5-5.5hrs from the time he wakes & bedtime about 5-5.5hrs from the time he wakes from nap. I do believe that 10pm is quiet late for bedtime & if its any later than that then its really cutting his night short... hence more overtired & more night wakings.
So I would try to bump lunch up & aim for something like this:
8.30 - wakes up
breakfast
snack
lunch
1.30 - afternoon nap (1.5-2hrs long)
snack
dinner
8.30 - bedtime
You could do this gradually (weaning the night feeds) or cold turkey.
Here's a link to Gradual Weaning:
https://babywhispererforums.com/index.php?topic=52857.0& if you want to go cold turkey:
https://babywhispererforums.com/index.php?topic=63896.0Alot of babies don't need a night feed past 12months but how you want to do is is up to you.... you could say set yourself a goal of 4hr stretch... so if he wakes earlier than 4hrs into the night then you would do wi/wo or pd & then extend that to 5hrs (so no feeds until the 5hr mark), 6hrs, 7 until he is sleeping all night. He certainly doesn't need to be fed 40mins into the night & then every 1-1.5hrs thereafter. He is waking up at every transition (from deep sleep to light sleep, etc...) & using the breast as a prop to return back to sleep. Have a read through that link... I think she also talks about introducing an object or something that will help him with breaking the habit.
Yes it would be much easier for a male to do the night wakings & it would also be easier if you would wean altogether but you
don't have to wean &
can still do this on your own... you'll just have to be extra strong!
Good luck & let me know what you think.
We'll be here to help you get through this....
Layla