I always wondered this about other moms as well when I started babywearing. The place I wore him the most often was at home
(maybe b/c that's the place I AM the most often! haha) I would wear him while vacuuming, doing dishes, making meals, playing with other child, even folding laundry. If going out and about, I would put the wrap on before we left home (or throw on the sling once we got there) and wear him grocery shopping and anywhere I was going to be for more than a quick run in and get out kind of thing. I think a lot of it depended on where he was happiest at the time, if he was sleeping, if he needed to nurse, etc. (like if he had just fallen asleep in the carseat, and i was running in somewhere to pick up/drop something off for 5 seconds, I would leave him in the carseat and hook it into the stroller so he wouldn't have to wake up and then struggle back to sleep again in the car.) I have one bit of advice though...if you are going to ever carry your LO in the carseat carrier, I would really recommend hooking it into the stroller. It's horrible for YOUR back to carry the baby like that - it's so awkward to hold, etc. AND babies always get so knocked around and such when being carried like that. It's not good for either one of you. I guess I would say I always tended to wear him unless it was one of those instances like I mentioned above. Good question, though, and like I said, I always wondered the same thing
In the end, it's whatever you and baby are most comfortable with and happiest with.