I've used the smoothon urethane and silicone rubber molding stuff before it can work well but you need to follow the directions to the T.
Depending on the urethane you'll have to degass it or you'll end up with bubbles in the casting (ask me how I know). You can actually build a pretty quick de-gasser for not very much $$. I used a few air fittings and a vacuum pump that I use for AC work. I just hooked them to a glass mason jar type thing (I think it was a spaghetti jar from WalMart or something)
When you mix your ingredients you put them in this jar first, apply a vacuum and you'll be amazed at how many formerly invisible bubbles appear, and then when the foaming is done you do your casting.
I've designed a few parts for injection molding, and I've done some casting which is I believe what you're thinking. your part is probably going to be next to impossible to do as one part. If it was me I'd make a mold for the round parts, you can do a mold with 3 cavities or more if you want to speed up the process. I'd position the part with the large diameter facing down in the mold, and make 1 half of the mold cast the large diameter and 1 half cast the smaller diameter. This was you can position the parting line somewhere were you may not have to finish sand it afterwards (towards the back of where the large diameter meets the small diameter). You could then make another mold that you would put the 3 circular parts into and cast that block onto them. Judging from your pics you're already doing that though?

But with urethane you should have a peg in each piece for the casting to mold around to form the block since new urethane won't want to stick to old urethane.
For making the parts easy to remove from the mold you would generally have a 3 degree draft angle on a part like this (it basically ends up looking like a cone) but can be done without it if you use a really tough silicone mold. You'll probably end up tearing through a few of the molds though since it looks like your part doesn't have a draft angle on it so in the end it might not be very cost effective to mold the parts, but at least you'll learn a new skill.
When we make masters for stuff like this at work, we usually have the master that the mold is going to be made from 3D printed (check out shapeways.com) for cheap, and I mean cheap 3D printing. I honestly can't figure out how they make money, I've had parts printed for me in the past that ended up going into the 1000's qty before we made a mold because it didn't make financial sense to tool up a real mold they were so cheap. Their finish on the cheap stuff isn't so great though, so for a master mold you usually end up spraying with high build primer and sanding until it's absolutely perfect. You may also find that you like the texture on your parts. I don't think I've ever done a part without texture since you see finger prints on them if you don't have at least some texture.
Hope some of my ramblings help. Good luck