The section on tools in the front of every Haynes auto repair manual is wise. Buy cheap when you need it. Buy sets when it truly benefits you. Not just "oooh, a deal!" Replace cheap with better when cheap fails to do what it needs to do.
An example My HF blind hole puller didn't do the job on a bearing race (it had done fine dozens of times. I ordered that size in OTC.
My snap-ring pliers and lock-ring pliers started as Craftsman. I now have Snap-On and Matco. This was because of tool wear, slippage and time wasted.
Other times, expanding what you have helps so you don't have to run around chasing tools. A spare breaker bar and 1/2" sockets for the trunk, duplicating some you have in the garage, certainly.
I like SK because I grew up using them and have had my own for nearly 20 years. They have been durable. I have Taiwan and China tools, certainly.
Buy when you need something and buy what suits your budget. If you buy 100 items cheaply, and upgrade 15 to higher-priced later, you are money-ahead than if you bought all 100 at a higher price point originally. This is an economics thing; spend over time, instead of at the beginning.
There's so much more to product selection than buying based on brand. Learn what screwdriver handles you prefer to use, what ratchet handles work best for you etc.
Since you're asking questions instead of outlining what you need to use them for, start with a mega set in a Kobalt or Stanley that get you started and supplement from there based on need, preference and budget. There's no one brand solution, but as a starting point, that's a reasonable thing to do.
