yes you are right about the part on looking as though to go fight war it's a matter of getting used to (IMO). when i first started bringing baby out i was skeptical if i should or if i can get anything done. after some time, i simply got the 'hang' of it. i prepack my bag to use anytime
i bring the same stuff as you other than the bottle of EBM, if my girl's hungry i just direct latch on. easier n less 1 item to bring (n 1 item to was after the trip ) I'm just lazy
I would usually pre-plan my route or things i want to do before i leave the house, then deciding if the stroller, carrier or pouch would be more appropriate. Though personally i prefer using the pouch (similar to sling). my baby likes to KPO and thus cannot put her totally in the pouch covered or she'll make noise so i tend to put her head outside when she's awake and thus like you supporting her head. once she naps, i put her inside.
not sure if you feel the same way as i do, but when i see my girl in the pouch, i feel that she's all squished/squashed up inside, and looks uncomfortable but somehow she can sleep inside. I wonder if she's really comfortable or maybe i'm just not good at using pouches. hah