Wow I'm not surprised you feel like you're making meals all day! I remember feeling like that just with DS never mind with 2 who are eating out of sync with one another!
I think I'd try:
- 8.00 breakfast keep
- 10.00 DD2 milk keep
- 11am switching lunch to a snack (possibly with sippy of milk), so she is hungry for lunch
- 12.30 lunch for both
- 1.15 milk for DD2 before nap keep
- 3.30 offer DD2 snack along with DD1
- 4.30/4.45 split the difference between the times and give both dinner (DD1 only eating a little earlier, DD2 may be able to hold out as she's had a snack an hour or so earlier)
- 6.15 milk DD2 keep
This keeps 3 good milk feeds (although you might find the pre-nap milk reduces if she has lunch later than she is used to, this should be ok if her daily milk intake is reasonable), 3 solids meals and 2 snacks.
With some of the bigger changes in times you could move it in increments for DD2 if you feel you need to. For instance she might just agree to a snack at 11 and then wait until lunch at 12.30. If not though you could do a small snack at 11 then lunch at 11.30, a day or 2 later do a small snack at 11 then lunch at 12, 2 days later snack at 11 and lunch at 12.30.
I didn't see a morning snack for DD1, maybe there isn't one, if there is one I would get both snack times in sync.
What do you think?