I have a mix of tools from Snap-On, Matco, Craftsman and yes, also Harbor Freight.
In buying tools I don’t run to the Snap-On or Matco truck and spend $40 for each screwdriver. Instead, I decide the quality needed in the tool, and the frequency of usage. For example: I don’t do a lot of heavy truck, but do occasionally, perhaps once or twice a year. Having a one inch drive socket set through Snap-On would easily cost me $2000. The Craftsman set was only $600 and came with more sockets. This suits me just fine. On the other hand, if I was doing heavy truck every day, I would probably opt for the Snap-On or Matco quality. This is how I purchase all my tool and thus my tool box is a mix of all different brands. I do not feel it necessary to have a loyalty to any single tool manufacturer, as manufacturers have different design tools and different warranties that suit me differently. Even Harbor Freight. I don't do much battery work, but needed a battery carrier. The $6.95 battery carrier at Harbor Freight did just fine for the one or two times I need such a tool.
When I was teaching automotive; Snap-On offered my students a very very heavy discount on tools and boxes. They were trying to lock in my students to their brand of tools early in their mechanic life. Not a bad idea, I even picked up a few tools this way. Most colleges have this type of arrangement with a tool company. Almost worth taking an automotive class just to get the tool discount.
I feel that 'overall' for a box and good assortment of tools, you can’t beat Craftsman. If you start calculating the price compared to Snap-On, Matco, and others, you will see that you get the biggest bang for your buck at Sears, not to mention Sears credit and better warranty on their tools. Yes, Snap-On and Matco also have lifetime warranty, but the difference is that Snap-On/Matco guy will stand there and argue with you about a cracked socket, claiming you used it on an impact gun, or something else, often denying your warranty. The lady at the Sears register will happily exchange your socket for another all day long. Purchases and exchanges are much easier at Sears, especially if you work on weekends and holidays. Many Snap-On/Matco route drivers take weekends and holidays off leaving you without tools until the next work day.