So here I am.

Carseats/strollers: We went through a number of them, and by FAR my favorite one for portability, ease of use, and practicability was the Graco Ultima TS (picture: http://www.muccelmic.com/images/GRACO/graco_ultima_ts_autobaby_gasha.jpg) I realize you probably have slightly different models in the States, but I’d like to point out a few features:
1. No cup holder for parent or child. ;)
2. Seat can be reclined almost to a horizontal surface, so unless you want to place a newborn baby belly-side down on it, it will be serviceable from birth to toddlerhood (we still use it for Zsuzsi, and she’s past 3). And even if you want to put the baby belly-down, you can always even out the surface with a folded up blanket and voila. Even surface.
3. Lightweight, easily maneuverable, AND folds up small enough to fit in the trunk AND has a huge basket to pack stuff into. This was important to me because I go shopping with it on foot to the local stores and markets.
4. One-click system for attaching the carseat, which is sturdy but light enough to carry in hand for short distances AND is easy to strap in without a base (which is also available, btw). Also, Vivi used it til she was 18 months old, granted, she was a relatively small child. So we got good use out of it.
5. Cheap.
6. Did I mention no cup holders anywhere? Nor digital clocks, thermometers or heart rate monitors.

Carriers: The Moby Wrap may look undignified, but again, having tried literally a dozen types of carrying devices, I must say that the Moby Wrap is the most comfortable one for smaller babies, with a Didymos or similar style non-stretchy, but light wrap the most comfortable for older ones. It’s worth the time and money to attend a sling-tying class if one is to be had near you. I carried my girls past age 1, and I wish I had learned how to do a back carry way earlier than I did because hands down it’s the most convenient way of carrying them (unless I’m going shopping, then I take the stroller). If wraps are too fiddly for you, for smaller babies, Baby Björn or ErgoBaby carriers are also pretty good, but really not anywhere as comfortable and easy on your back as a wrap. I also had one of those metal frame backpacks and I did a lot of research, and got a relatively pricey one and it was SO UNCOMFORTABLE. For both of us. Now that may just be bad luck, but you have to figure the weight of the thing itself is often considerable, too, and you’re only going to start using it when the baby is relatively older to begin with. My point is: they’re bulky and heavy, and about the only good thing about them is extra packing space, which you don’t have with a wrap. But I doubt you’d want to carry even more weight after you’ve got the weight of the carrier and the weight of the baby figured in.