For nearly 20 years I didn’t have to do much business travel. These days life is different. When my trip frequency rose above once per month I evolved a bag strategy which is both imperfect and functional. It is also very heavy on the Tom Bihn gear, because I like his bags and I tend to stick with things that work well enough. Other companies also make great stuff; my former boss swears by WaterField bags, for example. Choice is awesome.
My general theme is simplicity. Painless packing is the single most important aspect of this whole thing so keeping it simple is important. Particularly when it comes to cables, I’ve often just bought an extra cable so I don’t worry about remembering to pick one up and carry it with me. This is useful to me because I’m really forgetful. I am, obviously, fortunate to be able to make that tradeoff.