On the hole cutting. Whatever you do, DO NOT get
this type of adjustable cutter. I got it in home depot and tried it simply because it has the dust shield like the expensive ones, but it STINKS and I promise you it will mangle your holes. You will curse it halfway thru your first hole.
This type with a small knife like blade may work better, I don't know, but its more like the pro style hole cutters.
This style will likely work pretty well too. I tried the first one simply because of the dust shield. If you require a dust shield, spend the $100+ on the pro model. As for me, I went back to my tried and true dremel. Using my dremel with the hole cutter guide the holes were very fast to cut and came out perfect. They always have its just I always got a face full of dust. This time I learned a tip, cut in the opposite direction (counter-clockwise I think) and there is virtually no dust! It mostly shoots up into the ceiling instead of down onto you. Personally I would invest in a dremel before a good hole cutter because you will get so much more use out of it.
On the conduit, it will be impossible to use EMT except for the riser from the switch to the ceiling space. If conduit is required, the flexible Greenfield will be your only option that I can see and in that case you don't need to worry about any bending, etc. The reason for this is that the remodel cans have the electrical box on an arm and you need to bring the wire out thru the hole and wire it to the can then insert the whole thing back into the ceiling. That will be near impossible to do with rigid conduit. At least with the Greenfield you will have the freedom to toss it around like romex. But, I don't know the codes in that State, so check with your local AHJ.
Edit: Always happens, I started typing this before CORT's previous post, so my comment about conduit are redundant.