I've been buying tools my entire adult life, and I've sampled about every brand under the sun. I shop based on quality, ergonomics, availability, innovative designs and useability. Somewhere pretty far down the line is cost. I don't really care what my tools cost as long as they're what I want. Sometimes I want the best of the best, buy it once tool and sometimes I want the disposable option.
I never have regretted buying good quality tools. I tend to prefer USA, Euro and Japanese tools. I'm not particularly brand loyal, but I do default to Snap-on as the gold standard. I pretty much only buy hardline hand tools from them, but I've yet to find hand tools I like more. Snap-on sells a lot of mediocre tools and even very nice at a very high price to unsuspecting mechanics, and if you know what ones to avoid, that helps a lot. All the tool trucks do it, not just SO. Welding helmets, power tools, shop equipment like blast cabinets or air compressors, stuff like that is a HORRIBLE deal from the tool guy. When I graduated high school and was headed for welding school, my grandma gave me some money to buy a new welding helmet. I ordered the nicest one the SO man could get thinking it would be the best one money could buy since it said Snap-on on it. After all, this was true for my ratchets and wrenches I bought and loved. I was PISSED when I got it in and I took one look at it and saw it was just a re-badged Jackson painted red. That said, I still have and use that helmet occasionally and it has been great, but I could've bought an IDENTICAL one for HALF the money.
I regret buying Craftsman. They almost all ended up getting replaced with another brand. I've been disappointed by CM tools a LOT. Especially the screwdrivers, ratchets and smaller sockets and hex tools. I don't own much from HF, but the stuff I do own is pretty bad. I won't go there unless I have no other options. I still am glad we have a HF in town, they've saved my **** a few times, but 95% of the stuff I bought there broke pretty quickly or is so poorly made I don't want to use it unless I have to.
If I could go back in time and do it again, I'd still buy SO, Mac and other high end truck brands for my core hand tools, but I'd avoid the tool trucks for anything not hand tools and avoid anything they rebadge. I'd buy a lot more industrial brands for things like sanders, impact wrenches, etc. I'd also just buy a triple bank toolbox right out of the gate. I've "upgraded" toolboxes a **** ton over the years, I'd be much better off just buying one and done.