The 640 & 60 are too heavy to pocket carry, IMO, so Bob needs to plan on getting a good belt and holster. A good, sturdy 1-1/4" dress-style belt will be sufficient to handle either of these. As for Bob's other "choices," no comment.

If Bob is planning on pocket carry, he either better be a big dude, wear sloppily fitting clothes, or look to something less powerful, smaller, and lighter - probably an autoloader in .380.