My suggestion is to start out organized.....and keep it organized...
The more tools you get, the harder that is to obtain. I just started re-organizing 15yrs worth of tools. It is a massive PITA.
Whatever brand you get, get one with a lifetime warranty. Personally I own a bunch of older craftsman and some Kobalt. I prefer Kobalt to much of the newer craftsman stuff.
I'm very careful with what I buy @ HF...It's a personal preference, if it's getting a bunch of torque on it, I don't want it to break. I've broken tools and hurt myself pretty badly. (this is not to say some of those weren't "high end" tools...it's just less likely with a slightly better quality tool.) Also note that I've beaten HF's prices at places like Northern Tool. (and got a better product). Watch the sales and use your coupons
Disclaimer, I'm a huge fan of HF's 42-44" tool chest. IMHO if you're wanting a nice box for less than a grand, buy it. I've got about 600 in my bottom and top boxes combined. they are a very nice product.
Must have's:
1. Gear Wrenches.
2. electric impact driver.
3. nice torque wrench (at least the 1/2" drive)