RE: Good gawd, why can't I just pick a sling? Help!
Well, just to add another opinion to the mix, LOL....
I would get either a Mom and Me hemp pouch or a Maya Wrap. I love how soft and easy to use the Maya is. (FYI, I also have a Zolo and just prefer the Maya). I use the Maya to carry my 30 pound two year old with no problem. Others prefer the Zolo, and I also have a Zolo, but the Maya works better for me. I do think that the Zolo is easier to use "out of the box", but for me, the Maya is the more comfortable sling. I did have to watch the video that came with it to learn to use it properly.
And even though he's 27 pounds now, he may not necessarily gain a lot of weight in the next year. My DD was around 20 pounds at 1 year and only recently hit 30 pounds.
FYI, I am about your size and I wear a small Maya or a small Zolo.
Beth, mom to older DD (8/01) and younger DD (10/06) and always missing Leah (4/22 - 5/1/05)