A great steak doesn't necessarily have to come down to how much you spend, but rather more than how you prepare it (within reason). And preparation depends on the cut.
Steak is graded into three general categories: Prime, Choice, and Select. This has to do with how the fat marbles through the beef.
The least common is Prime, but it has the best marbling and the highest price. The better fat is distributed throughout your selection of beef, the juicier and more delicious it will generally be. Hanger fat on the edges doesn't put juice in the meat, marbled fat does.
How fresh is the beef you're buying? Dark blood means old. Cloudy blood means old. If it's transparent and bright red, it's generally fresh.
How does it smell? If it smells bad, it probably is. Fresh kill will generally have a slightly sweet smell. A butcher can help you with learning that smell.
Intentionally aged meat will have a more dark purple color to it than old meat, which is generally browning/graying on its own. Aged meat can ramp up certain flavors in the beef because it removes water, and there are ways you can age this at home if you have the space and time to dedicate to the procedure.
I'd advise against kobe beef within the US, as it's not really kobe beef.
There are rules and other aspects as to why, but like with most foods in the US, there are ad words to entice sales and up prices. Ad words on your food are bad (see things like "certified organic", "low fat", "great source of omega-3s", etc). The exception to this might be with Certified Angus Beef, as the certification is done by an independent panel. Granted that panel is somewhat tied to Angus ranchers, so there may still be a little bias there. But you can lookup the grading points they look for on Certified Angus to see if that's something you might be interested in. Note that Certified Angus isn't the same as Angus. There is nothing special about Angus, it's the certification process that sets it apart from other meats.
Organic with beef doesn't really apply the same way as with vegetables. What really plays into the flavor is what the animal is fed. In general, cows are fed dent corn, and allowed to graze on natural grasses (in the Midwest). In California, they are most likely fed only corn and pellets.
Corn tends to fatten up animals quickly, as it does with humans, so what you are looking for is something fed totally, or primarily, on grasses. There is also a counsel that certifies this. There is also grass finished beef, which just means the cow ate grass while it was waiting for slaughter. Is the flavor difference really that noticeable? I think that depends on your palate and preference. It does cost more, so you'll probably take that into account.
Regarding cuts, most steaks come from the loin and the butt (shoulders) of the cattle. There are plenty of other cuts from a cow, but they are best prepared as roasts, ground for burger, turned into stews, etc.
For pan frying/grilling you'll want cuts from the loin or shoulders. These include all the common steaks you grew up hearing about like sir loin, flat iron, porterhouse, t-bone, rib eye, tenderloin, etc. You'll generally also see steak cuts of round for cheap. Round is simply the buttocks of the cow. Round also has less marbling, so it'll tend to be a drier steak.
There's a great video to show you a pan frying method (if you have access to an oven) here. You want to taste the meat, not the marinade (at least with pricier cuts), so stick with grape seed oil, sea salt, and fresh ground black pepper as a rub.
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