Lots of questions (related to this Meta discussion). I will just tackle a few points I feel confident about answering.
Subfloor
The Schluter DITRA does not need to be on CBU so I would skip the 1/2" layer of cement board you are planning on using and make your plywood subfloor thicker (or just skip the CBU and keep your 23/32" OSB). CBU is not "stiff" enough to be a subfloor, it can be used instead of DITRA but it must be secured to a subfloor. It rarely makes sense to use 1/2" on the floor unless you are trying to make the finished floor come out to some specific height (for example to help the transition to another room with a different floor). If you are not goin gto use DITRA, you will want some CBU on the floor but the 1/4" stuff is fine.
Apply the modified thinset and DITRA directly to the plywood subfloor. Checkout Schluter's DITRA Installation Instructions for details on the subfloor prep and how to secure to DITRA to the plywood.
Toilet
Without a picture or diagram it is not really clear to me exactly what the issue is with the toilet drain, but that won't stop me from taking a guess :)
You may be right about getting away with cutting a larger hole in the subfloor to handle the bend of the toilet drain pipe. Are you sure the PVC drain will stick above the finished floor? Realize that the thinset between both the subfloor/DITRA (not very much) and DITRA/tile (more so) will add a little to your height, maybe between 1/8" to 1/4".
Have you measured the height of the toilet drain with the flange installed (just dry fit it to take a measurement)? The flange can be installed on the top of the finished floor (tile), on top of just the DITRA, or on top of the plywood subfloor. In your case you would probably want it as high as you can, so install the tile first and then glue the flange to the PVC closet bend. I think once you dry-fit the toilet flange you will see you are OK here.
Cut slots in the concrete close together with an angle grinder and diamond blade, knock off the little ridges you have just created, and then either flatten with a cup grinder or level up with compound.
Best Answer
I've done things like this on a number of occasions, and the problem is that you'll create more bumps than you resolve. Only the inner portion of your depressions measures 1/8", and fairly quickly they taper up to a smaller dimension. This means that the edges of your shingles are almost always too thick for their position.
Also, they're crunchy. For at least a while after installation you'll hear it underfoot.
You're much better off skimming with a leveling compound.