Working Moms who have babies on medication...

I am going back to work on Thursday. On some days, DH will be with DS - others - my brother, a friend, etc.
Prevacid is a pain to give - although DS drinks it out of the syringe now - lol. Do you give it to your DC before you leave for work and then have the caretaker give the bottle. If DC is sleeping when you leave, do you have the caretaker give it? DH is a firefighter so he works 25 hour shifts. So, for the next couple of weeks, my brother will be watching the baby (hopefully) in the morning until DH gets home. We'll have about a two hour time period between when I leave and he gets home. I know my bro is a little nervous about watching him and I'm not sure I want to have to get him involved in the whole medication thing.
I asked the GI if we could wait until second morning feeding to give Prevacid (once DH was home) and he wasn't thrilled, but he said no later than 11.

Just looking to see what you all do...

Thanks!