Hi. I am no expert, but dd is almost same age. One first question... is he teething? Cruising may take some night sleep, and feeding, but teething is a mayor cause. I think as I see your schedule that from 7 to 1 he barely eats, and for the last 6 hours he can have lunch, dinner, and milk. 3 main feedings in less hours. How about feeding lunch at 12, taking out her afternoon bottle, do it at 3.
Something like this: Also some babies drop their 4th bottle almost before a year. Some of them, like mine drop even the 3rd bottle.
I will not mess with the 5 am bottle as I will recommend you to take it away by extending wakening time and feeding time, but I really do not know what to tell you about this. Maybe pd?
7 breakfast
9:30 snack
10 nap
11:30 or 12 lunch
2 nap
3 bottle
4:00 dinner
7 bottle
Cutting one bottle may put more ounces to the others or maybe not, but at this age their intake may be lower as he is really eating good amount of solids, even more than mine is... his dinner is very good so maybe he really feels satisfied.
As for covering him maybe he just does not like to be covered, and that wakes him up. Some babies are not as hot or cold as we are. Maybe try to put a grow bag or put more clothes under his jammies. What I do is instead of using a cover sheet in her crib is put a hot blanket as a sheet, that way under her it is a hot stuff... IYKWIM.
And about the sippy, he will take it eventually, he is still young for mastering it.
Practice a lot during the day cruising. Teething or overtiredness make babies fuss at bedtime so 60 min before bed lower activities. If everything is OK, try pd. Is he standing in his crib, and is able to put himself down? Be sure to know how much awake time he can handle, maybe 4 hours is a lot for him in the afternoon.
11 months is a very difficult age as they are leaning way too much at this age, and probably teething too. They want to become more independent. They reject being spoon fed so lend him a spoon while feeding. Put FF at his chair for him to eat.
You need to test A timings every day and see which one works, but if he is teething first you need to help him in that, and understand the consequences of it, and just go with his flow.
I hope I helped you somehow, I am sure more experts ones than me will help you even more. Please feel free to pm if need anything.
Good luck!!!