#2
This is a chord melody. No...there isn't software to do this(if there is make sure to tell me!)

He has an understanding of how chords and melody(the vocal line) are related. It is a discipline of voice leading. With this understanding he can construct the melody to take the lead over the harmonic background(the chords)

Look up the stuff in bold to get a glimpse of what it takes.
Gear:
Inflatable Guitar
Digitech GSP 2101/Mosvalve 962/Yamaha S412V
My Imagination
#3
I do it too, i just hear the voice and match it up on guitar, i have no idea what im doing all i know is that it sounds cool.

My things:
Bowes SLx7
Washburn WG587
Washburn X40Pro
Washburn X50
Washburn HM24
Washburn WR150
Laguna LE200s
Arietta Acoustic
First Act
Valveking 112
VHT Deliverance