The only reason to buy Craftsman vs any other brand is the lifetime guarantee, and that's only on hand tools. I personally don't trust that Sears will remain solvent for my "lifetime", so I don't feel the urge to pay extra for a guarantee that probably won't be honored. Similar with Snap-On, but the problem there is finding some place to get the guarantee honored.
As for Harbor Freight (and Northern Tool), if I find I absolutely need a specific tool for a project that I've never needed before I buy as cheaply as possible. HF and NT meet my needs. If I rarely use it, then no money wasted. If I use it enough to break it, then I research and buy a better one.