My buddy did it this way back when he did hobby boards. I thought it was insane but hes got infinite patience.
I use a drill secured on a bench/drill press - that allows me freedom of movement. The only thing I am missing is one of those affixed light sources shining down. But I usually turn on my living room light and the halogen light and thats enough illumination
hell yeah!
Depends on how careful you are. Without the bench/drill press - you are looking at wasting a lot of drill bits.
carbide is what I get - off ebay. I have about 5 containers of those 50 pack types with varying sizes from 17.7mil to 45mil. For larger holes and or holes for standoffs/spacers I use titanium drill bits
Good luck