Hi Yuri & welcome to wetpixel!
I've got both your lenses and a Canon 20D in Ikelite housing. I've used the DS50 strobe but just bought the DS125 and they all work well.
100mm Macro
I got the recommended flat port without manual focus and since it is specifically made for that lens it will fit just fine. There is also a model with manual focus option but I've so far not felt a need for it. That may be different if you are really trying to push the 1:1 magnification limit. Others will be in a better position to discuss this.
If you do decide to get a model with manual focus I wonder if it is worth getting a slightly longer port (5.5" model) because that gives you the option to add a 1.4x teleconverter and I don't think the extra 4mm will be much of a disadvantage during normal use. Is anyone using that combination?
18-55 EF-S
I've used if behind the short dome port, whatever is the recommended port on Ikelites compatibility table (#5303 I believe it is). That port can also be used for the Sigma 15mm fisheye which could be an interesting future lens for you. After the discussion about optical quality of zoom and prime lenses in another thread I must admit that I have been quite pleased with the images from this lowly kit lens. You want to keep the aperture closed to f8 or more but then the images are sharp and look great (at least if you're not yet spoiled by working with L class lenses too much).
Like bandit, most of the time I set the camera to manual with the shutter time fixed to 1/200-1/250 sec. You can then play with the aperture to control the amount of ambient light (blue versus dark/black background when shooting against water) and depth of view, letting the TTL work out the right exposure. I use shorter exposures then bandit but in reality the short burst of the flash mostly controls the exposure and (lack of) motion blur, so I've not found it to be a critical parameter.
Much of your success depends on being able to spot interesting critters or seascapes and mastering the skill to approach them closely without chasing them away. Try to get on eye level if that is possible without getting too close to the reef. Rocks, walls, and ledges that come up several feet or more from the substrate are often good spots because you can stay on the side and shoot objects at eye level which is hard to do on a horizontal substrate.
Good luck and enjoy the pleasures of UW photography!
Bart