Q1: They make a specialty spade bit with a small hole in the spade.
Drill the hole, run the wires through the bit, pull the bit back out.
You can also do this with a regular bit and a small amount of
electrical tape.

Q2: I hate plaster. If it were me, I'd find some way to route the wire
in the stud space, or mount a wireless phone instead.

Q3: Use these instead: http://www.tselectronic.com/3m/ug_ur_uy.html

Q4: See Q3. Or use:
http://comcables.com/ProductDetail.a...259&CatID=2542

Q5: You already answered your question. It's just a matter of how much
you want to fight the tool you are using for any particular job.