If those are both 'real' macro lenses (i.e. give a 1:1 image on the sensor) I'd go for the 100mm, as it gives a bit more working distance, so you won't be quite as much in the mouth of your patients
. The smaller closest focusing distance for the 50mm doesn't mean a thing
here: for a 1:1 image, you will need to get to 100 mm distance with a 50mm lens, compared to 200 mm with a 100mm lens).
As for the 50mm being lighter and smaller: both lenses have about the same maximum aperture (F2.8/2.5), so the 100mm will have a larger diameter and thus a lot more glass, and I guess the USM motor adds a bit of weight as well.
If you want to go easy, I'd suggest starting with the ring flash (or a system using 2 small flashes). As far as I know, your 18-55mm kit lens should be good enough for the web and small prints, the way you prepare your images will be more important (i.e. do the resizing to the final size yourself and don't forget to sharpen a bit afterwards).
Another point that might be important for you is colour management: some of the photo's you linked to are clearly of the same person, but colours are quite different between images. That's a whole different kettle of fish, and not dependent on your lens (ring flash might make it easier to get reproducible results though).
Remco