Help me decide! Please!

I have about $1,000 give or take to spend. Need a good lens for shooting outdoor family portraits (normal 4-6 people) and be able to be a good indoor natural light baby portrait lens.

I have a 40D & a 430 speedlite. I only have kit lens 28-135mm & the nifty fifty.

I'm looking:

17-55mm 2.8
85mm 1.8
50mm 1.4

open to suggestions. I'm ready to hit the "order" button at Amazon. I've looked at the photo archives & still can't just decide!

I'm still new & learning so I don't want to make the wrong decision, but I want a better lense!
Thank you soooooooo much!
Holly

Since you have a 40D, I recommend the Sigma 50mm f/1.4 for portraits. It is equivalent to ~85mm on a FF camera, which is a perfect focal length for portraits. It's also very sharp at f/1.4, which makes it a great natural light lens.

The 17-55 f/2.8 would be a good choice. You say you already have the nifty 50. You also have the 430 speedlite so you could the 17-55 indoors as well. I have read alot of good things on this forum about the 17-55f/2.8. I'm sure we all want more than we can afford. Have fun and enjoy your new glass!

For family portraits I'd think the 17-55 would work every bit as well as the 50 f/1.4. The advantage of f/1.4 is shooting low light and subject isolation. For family portraits you have to stop down a bunch anyway to ensure the subjects are in focus.

I have the 50 f/1.4 and while I really like the lens I've used it very little.