Bobby.T,
What version of ASME Y14.5?
Usual practice is for a flat head screw to make contact with the clamped part on the conical surface only. Unless you are doing something unusual, it seems more appropriate to use the conical surfaces as datum features for your part. Why do you intend to use the cylindrical surfaces?
Is that a "no" to the fourth question? Without some idea of what the various features on the part are supposed to do, it's hard to tell whether they might be toleranced appropriately.
As for general advice, first I'll point out that there is a difference between a datum feature and a datum.
I think the whole concept of datums and datum reference frames as defined by ASME Y14.5-2009 is an unnecessary distraction, so I generally ignore it. All that really matters is the relationship between the actual part and the theoretical geometry, and the constraint of that relationship by contact between datum features and datum feature simulators. This idea is discussed in thread1103-451664, from which I copied the previous two sentences.
pylfrm