We need more information to answer the first two questions (ground conditions, drill depth and orientation, grouting technique etc). What is it exactly you are trying to do?
To answer your third question, hollow stem augers do not like rock, concrete or rubble. I've drilled through silt-sand-clay stone using continuous flight augers with a large rig with lots of down crowd but not anything extremely tough,,, and not with hollow stem augers, which inherently have a greater diameter than conventional CFA therefore require more volume of the drilling obstructions (rocks/concrete) to be removed by the auger flights.
If you are looking at using the hollow stem to enable putting a grout pipe or some other product down hole then look at using one of the many duplex type systems available. Rotary percussion with either top or bottom hammer to get through the given drill obstructions to advance your casing to the desired depth. Once at depth, one can trip out the inner drill string leaving you with a cased hole.
Which ever system you choose, I'm sure your driller will ever so politely let you know on the quality of your decision.