Hi J.,
This may be long so bear with me, lol.
I think 1 problem will solve the other eating = sleeping
OK, First thing the food......here is what I would start with
Breakfast:
fruit puffies, cheerios (also promotes hand an eye cordination)
Toast, biscuits, waffles, pancakes, frencn toast sticks (extra butter makes it nice and soggy, easy to chew - no syrup), fruit cups, bananas sliced, applesauce
Lunch:
mac and cheese, mashed potatoes w/butter (instant are easy for now), cheese sticks, deli sliced turkey/ham, pizza, bread sticks, grilled cheese, spaghetti any kind of noodles, noodles of any kind, soup (I like to take crackers and crunch them up in the soup and it soaks up the broth), meat loaf, cheeseburger cut in small chunks, fish sticks, any canned or frozen vegetables, any canned or frozen fruit, bananas, fruit cups, applesauce
Dinner:
Anything you are eating for lunch or dinner he can have - make sure it isn't to spicy for him and cut it up in small chunks. If he can eat it you can eat it - with in reason of course.
For snack: crackers, animal cookies, pop tarts, cereal bars, dry cereal, fruit puffies, add in a fruit cup, anywhere in her you could add yogurt or yogurt burst cheerios.
Now as far as the sleeping make sure his daily routine is the same every day for example:
Breakfast 7:30 am a bread, fruit and a bottle or sippy cup of milk
Morning nap 8:30 am - 9:30 am or 10:00 am (if needed)
Morning snack 10:30 am milk and a snack
Lunch 12:00 noon - 12:30 pm a main dish, fruit and veggie and milk
Nap 1:00 pm - 3:00 or 4:00 pm
Snack 4:00 pm or when he wakes up a fruit or juice and crackers or cereal one of those
Dinner 5:00 pm - 6:00 pm main course, fruit and vegetable and milk
playtime 6:00 - 7:30
Bedtime routine starts around 7:30 - 8:00 you may eve ad in a small snack before bath time
Bath, Bottle and milk again, Book, Bed your goal for bedtime would be between 8:30 - 9:00
I think eating more will help him sleep more. Try for 1 long nap then 2 small naps. It's possible that when he is waking up he is still exhausted but he is also hungry so the 2 are fighting each other. Now the routine that I out up top may not jive with what goes on in you house hold so tweak it to your needs. Idealy you want him up more during the day then at night. You want him to be ready for bed with in a couple hours after of eating dinner.
Also to get him to go to sleep on his own - whatever you are doing now .... keep doing it but cut it down by 5 minutes each naptime and/or bedtime. To where you only hold him for 5 minutes, give him hugs and kisses, lay him in bed and say good night, turn out the lights and walk out. Don't walk back in unless absolutely necessary and try at all cost to not pick him up. If you do have to walk in there let him no it is "bedtime". And when you lay him down at naptime let him know "naptime" he will begin to understand nap time is shorter then bedtime. Be consistent with and it should work. All of these things work together ....eating = sleeping = happy baby. W. B.