I am basically thinking that in terms of doing portraits that the:
Sigma 50mm f/1.4
is a leap in quality over the
Canon 55m f/1.8
which is a leap in quality over the
Canon 18-55m zoom lens
Am I on track here?
Yes. 50mm f/1.8 though, not 55mm f/1.8.
I have never used the Sigma 50mm f/1.4, and I own the Canon 50mm f/1.4 and have owned the f/1.8 in the past. I also have owned the Sigma 30mm f/1.4. I do not see why so many people slag the Canon 50/1.4; it is not a bad lens. Yes, the AF motor gets annoying, and yes it's fragile compared with the 85/1.8 (which I also own) but overall it is still a worthy step up from the 50/1.8 IMO. I use it wide open all the time and have never noticed a lack of sharpness. Of course, I think that the Sigma 50/1.4 would be a worthy step up from the Canon, but Sigma has its share of QC problems (front or back focusing -- have to send the lens in to Sigma to get it calibrated). I really enjoyed my Sigma 30mm f/1.4 and would recommend it to anybody who owns a crop body, *before* getting an expensive 50mm (but after getting the 50mm f/1.8... the 50mm f/1.8 should be everybody's second or third lens). The Sigma 30 is around $100 cheaper than the Sigma 50, IIRC, putting it right in line with the Canon 50/1.4.
BTW, here is a short explanation on what the aperture actually means. It is a measure of how much light the lens lets in. It is expressed as a ratio in terms of the focal length. A theoretical 50mm f/2.0 would have an aperture that is 25mm in diameter. A theoretical 100mm f/2.0 would have an aperture that is 50mm in diameter, while a 100mm f/4.0 would have an aperture that is 25mm in diameter. Multiplying the aperture by the square root of 2 (i.e., 1.4) results in a lens that lets in half the light; i.e., an f/2.8 lens lets in 1/2 the light of an f/2.0 lens, which in turn lets in half the light of an f/1.4 lens.
I have been saying "an f/2.0 lens", but I mean any lens at f/2.0. A lens can always be "stopped down" from its maximum aperture. An f/1.4 lens can be set to f/2.0 to deliberately let in half the light, or f/2.8 to let in 1/4th the light, or f/4 to let in 1/8th the light, or f/5.6 to let in 1/16th the light, or f/8 to let in 1/32nd the light. To get an equivalent exposure with all of these f-stops, you would have to adjust the ISO and/or shutter speed to make up for the smaller aperture. (Note, smaller aperture = bigger number.)
The amount of light coming into the lens is not the only thing determined by the aperture. Aperture also determines the Depth of Field of a photo (for a given focus distance and focal length). This is basically how much of the photo is in focus. Say that you have a 50mm lens focused on a subject that is 5 feet away. If the aperture is set to f/1.4, the "in focus" part of the photo will be a narrow sliver, from 4.92 feet to 5.08 feet -- roughly 1 inch on either side of the focus point. So if the focus point is on the tip of a person's nose, their ears would be out of focus because they are more than 1 inch back from the focus point. If the aperture were set to f/5.6, the depth of field would be from 4.7 feet to 5.34 feet, or around 7 inches -- easily enough to get a person's whole face into focus. Note that the focus point marks a plane, parallel to the back of the camera, in which everything is in focus. So you can take a photo of a flat piece of paper against a wall, and even if your depth of field is very small, the whole thing will be in focus as long as the camera is not tilted with respect to the wall.
Focus distance (distance from camera to subject) and focal length (length of the lens -- 18mm, 55mm, 250mm) also affect the depth of field. Closer distances give less depth of field -- given the same settings and lens, depth of field will be greater as you move away from the subject. At one point the depth of field becomes infinite -- this is called the hyperfocal distance. If you focus on a subject that is 100 meters away, even with an f/1.4 aperture, your depth of field will run from 150 feet to infinity. The focal length of the lens also affects depth of field. A wide-angle lens will give much greater depth of field than a telephoto lens. Using a 17mm lens with f/4 aperture on my 5D, the hyperfocal distance starts at 8 feet -- in which case, everything from 4 feet to infinity will be in focus.
Now you have some terminology... if you're curious you can google "depth of field calculator" and "depth of field examples" to find out more.