I started out with Craftsman tools. I remember day dreaming about buying those big kits they had in there catalog back in the 80's. I really enjoyed those catalogs!!!
Today I'm pretty much just buying the Kobalt brand tools from Lowes. I've never had one break on me, and they all work flawlessly. I retired my Channel Lock set of plyers because the long nose broke on my and the pliers always bind up on me. The Kobalt are smooth and flawless.
For big wrenches, which you probably don't need to get him until he buys his own tractor, I've found that they all work the same once you get over one inch. Tractor Supply has a good selection to choose from, and I have all of them up to 2 inches.
I have a few Proto sockets for brush hog blades. They are too expensive, but they where the only brand I could find when I needed that size.
I won't buy anything Craftsman anymore. They have gone full Chinese junk and what I did buy when they started selling them at Lowes, all failed quickly.
I also don't like anything Harbor Freight. I tried them awhile ago, and it was too expensive to spend the time to buy their stuff, to have it fail, and then to have to spend the time to go buy a better quality tool in order to fix what I need to fix.
If Home Depot is closer, I think their brand of hand tools is just as good as the Kobalt at Lowes. I have a few of their sockets and they have held up without any issues.
The older I get, the smaller I want my toolbox to be. I'm more into specialty toolboxes now, with the tools to do that task in each toolbox. For my hand tools, I use a small fishing tacklebox from Walmart that's bright blue, about a foot long, and able to hold exactly what I need. I refuse to put any extra stuff in there, so it's it's always light and easy to carry into a job. I have bigger toolboxes with bigger tools, and extra stuff like bolts and odd sizes screws in it, but I rarely take those boxes into a job.