Only generic apparel can have ballistic weave. Unique items like Kellogg's outfit can't. The most you can gain with ballistic weave is by adding it to an undergarment and a hat, giving you 220 total damage resistance. This is in addition to the arm, leg, and chest armor that you wear on top of them. A full set of heavy synth armor modded to the max gives you another 140 DR, a total of about 360.
Not true. There are several unique armors one can weave. Lorenzo's suit for one.
http://fallout.wikia.com/wiki/Ballistic_weave
Me too.
I would upgrade the Drifter's Outfit and wear that. I think it looks pretty cool. I would also upgrade the Silver Shroud suit and hat. Or at least the hat.
I think the concept is probably to do with going incognito. Being a RR agent, but looking like everyone else. For example, Deacon (the clothes horse ninja) is always swapping out to some different outfit that I presume is armored up with BW.