I'll throw my vote in for both a stretchy wrap and a pouch.
Both dh and I have tried to manuever ds into our Maya Wrap and he (and us!) just can't get comfy. It's SO easy just to pop him into the Hotsling. Dh hasn't given in yet, but I think he wants me to get him one in his size. I may just surprise him w/ a early Father's Day present.
We have a Moby Wrap too, and it's great. Ds tends to get fussy in the pouch if he's really awake - in the Moby, he can at least turn his head and look around. (Ds will be very happy when he can face outward!)