Bottle transition?

TLDR; Please give me your recommendations for a replacement cup at night.

So admittedly we’ve hung on to the bottle a little longer than we’re supposed to. It’s so hard to change something that works for bed time. However, it’s got to go. We only give our son 1 bottle and it’s at night right before bed. We want to transition him to a more oral friendly cup, if you will, for his last bottle at night.

During the day he uses the Dr. Browns straw cup which our pediatrician said was fine/great. We’ve been struggling with the cups that you turn upward to drink out of but we’re working on it.

We have had a little success with the other Dr. browns transitional bottle/cup that has like a flat nipple at the top but it seems to come out too fast. From birth he has had some feeding difficulties and choking/aspiration but it’s gotten better as he’s gotten older. It does make cups difficult to find that slowly give him a free-er flow.

Right now I hold him while he drinks his bottle then place him in the crib for bed.

For context he is 16 months old.