Does it come with carrying sleeve?
Yes, it comes with a long sleeve with shoulder strap.
I see it looks great for the sun as a shade umbrella, but how is it for rain? Is it waterproof like a regular umbrella?
Yes, it is waterproof and sturdy to withstand wind gusts.
Is this umbrella big enough for 2 people or guys with wide shoulders?
Yes, size 47" measures 39" in diameter, size 62" measures 52" ard size 68" measures 59". They definitely huge.
Does it fit in the umbrella holder for golf cart?
Yes, handle measures 1.4" in diameter and 6.6" in length.