PLEASE HELP!

My babes will be starting day care when he's 1 (we have a few months). I'm starting to get get really panicked for a few reasons.. he doesn't take a bottle at all. I'm trying to get him used to sippy cup instead so far he just chews it but does get some water out. At this point I'm not sure if it's silly to start him with a bottle or just keep trying the cups (and which bottle or sippy cup will work the best) . My biggest concern is I nurse him to sleep for all his naps right now unless he's in a swing or car. Im worried he will fight naps without me. Also I can't pump much at all (I'm going to try power pumping closer to the date. By then I know I can supplement with regular milk so I'll look into that if I can't get my pumping up). Any tips for any of this lol!