Have you tried one leg out in the anglepack?
You can use a woven wrap for all kinds of carries, well into toddlerhood. You can do comfy hip carries with a woven. You can do a hip carry with the ap, bit not nearly as comfy.
I love stretchy wraps, like moby's, for newborns. The lifespan of a stretchy wrap is about 15lbs (after that, it's just not a comfortable), so don't expect to be able to use one for a toddler. Mei tai are also nice, but I prefer the wrap for little babies (more comfortable to wear, easier to pop baby in and out, etc). I would start with a stretchy wrap, and then move onto a woven wrap (if you like wrapping) or a mei tai/buckle carrier with an older baby. Wrapsody...
I prefer a wrap with a newborn. I agree that it is a lot of fabric to deal with. For shopping, I tie the wrap on at home (under my jacket if it's cold out), and then pop the baby in once we arrive. This way I don't have to deal with the fabric, and the baby gets transfered quickly.
Well, it does depend on how cold it is outside. I try not to put too many layers on DS, because he gets plenty of body heat from me. Between the warmth from me, and the extra layers from the carrier, on most days that is enough. On colder days, or windy days, I add my monkey pocket over him. When he was very little, I would just wear DH's jacket over both of us, but now the pocket is the better option for us.
I prefer to wear DS next to my body. I don't like the feel of wearing a carrier over my big jacket. It's also much easier to have DS under my jacket, especially when going in and out of warm stores. DS wears a hat, pants, longsleeve shirt, sweater, and robeez. If I think DS needs to be warmer, I use my monkey pocket, which works really well!