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Beef is both delicious and healthy. 95% of the experience is based on the quality of the meat, but to the naked eye and the uninitiated, it can be difficult to tell the difference between a tender, delicious cut and a chewy, flavorless chunk of leather.
Because good beef is expensive, one is often tempted by cheaper cuts, which can lead to a bad experience. A strategic approach is called for.
Beef is graded, with Prime being the best (i.e. most flavorful with good texture and marbling), followed by Choice, then Select, then Ungraded (technically, there are also manufacturing level cuts that are irrelevant to this discussion).
It used to be that you could basically only get Prime at high end steakhouses, but we’re in something of a beef “golden age” and you can now get it from some butchers and stores. It’s very expensive, but sublime, especially if aged and cooked in an 1,800 degree broiler.
Choice is also very good (a steak from a nice restaurant that isn’t a steakhouse is likely Choice), not quite as expensive, and these days can be found even in some neighborhood grocery stores! This is the level that I like to purchase and consume.
Select or Ungraded are fine for certain preparations, like stew, roasts, or jerky. I don’t recommend this level for direct consumption off the grill or skillet.
The first thing you have to do is find a good source for your meat, that offers high quality & low prices. If you live near a Costco, you’re set… its meat department is miles better than any other in the industry.
Otherwise, I recommend evaluating all nearby grocery stores (I don’t favor butchers, because they are pricey and never have sales). You want a store that has a wide variety of Choice cuts, with aggressive weekly sales… always bulk buy on sale then freeze, if possible.
I'm not a fan of grass-fed... paying more for worse flavor has never been my bag.

For direct consumption, you want a steakhouse cut, or at least a “menu” cut:
Filet Mignon - most popular & expensive. Very tender; easy to eat, little visible fat or necessary knife-work. Light flavor so good with sauces. I like to buy a whole Choice filet at like $15/lb, then slice it up & freeze it. Otherwise, expect to pay $18+/lb. (Note: NY prices)
Strip (Shell) - very firm texture; easy to eat with fat mostly along outer edge. Good flavor. Individual steaks should be around $15/lb.
A T-bone is a Strip on one side with a tiny (or no) filet on the other. A Porterhouse has a bigger filet. I just got a dozen T-bones on sale for $6/lb, though the bone is dead weight. It does impart some flavor, though… the closer to the bone, the sweeter the meat, as they say.
Ribeye - heavily marbled with a lot of visible fat and necessary knifework, so not a cut for the faint of heart. Most flavorful cut, and includes the “rib cap”, which I consider to be the best cut of all. Like $15/lb.
The following cuts are not steakhouse cuts, but might be seen at the Chili's/Applebee’s level:
Loin Flaps - MY FAVORITE CUT. Tender, easy to eat, great flavor, and CHEAP, like $8/lb. Get them at Costco, where they are perfectly trimmed and abundant. If no Costco, forget it, it’s tough to find even at a butcher.
Sirloin - Like strip but not as good. At least it’s cheaper, like $12/lb.

Hanger - (note: not Hangar) very tender, great flavor, good value cut with interesting grain. Not that easy to prep. Around $10/lb.
Skirt - like hanger (which is the upper half of the diaphragm muscle, while skirt is the other half) but less tender, less flavorful, and cheaper. Around $8/lb
Flat Iron/Blade - new cut recently discovered via MRI analysis, popular at value restaurants. Very tender (almost as tender as filet), but flavor is mild and requires annoying knife-work.
Chuck Steaks - riddled with fat, not great, but edible. Probably like $6/lb., but I’d only buy it on sale at like $3/lb.

Cube Steaks - Tough, poor flavor, but cheap. Avoid, unless on sale for a song.
The following cuts are for recipes, not direct consumption. Never spend more than $3/lb.:

Top Round - This is my go-to at London Broil, beef jerky, or stew. Creates nice chunks of meat that soften nicely and is easy to prep.
Bottom Round - Top Round’s ugly sister, riddled with invisible gristle. Avoid, even for stew.

Shoulder “London Broil” - Inferior to Top Round, but acceptable if on sale.

Chuck - Fine, but again, inferior to Top Round.
“Mock Tender” - AVOID! It LOOKS like a nice piece of meat, but is tough and disgusting. Not even on sale.

Ground Beef - tough to grade, it really depends on who’s grinding it, so get it only at places where you trust the production values. Will pay up to $4/lb. If not on sale.
More thoughts on grass-fed:

It's really not as tasty, IMO. Grain-fed is fatter, i.e. more marbling, the source of flavor. Grass-fed just tastes weird, and any extra Omega-3s you get from it don't really matter if you're taking fish oil.

It's more expensive, to boot.

Pass.
Kobe beef (Wagyu) is an entirely different experience. It's so heavily marbled that it's comparable to pork belly. It's amazing in small portions, but too rich for an entree, imo. Also, it's UBER expensive.

An amazing experience, however, as long as you consume it properly.
The VERY BEST steaks, imo, are Black Angus/Wagyu hybrids (American Wagyu), typically available only at high-end steakhouses at ~$100/lb.

SO GOOD though. Perfect tenderness, flavor, & ease of eating. No Angus cut is perfect, always some sacrifice involved, but not with hybrid.
Oh, a little anecdote:

I was recently forced to endure a couple of months at Riker's. I was gonna a ribeye first thing back, but my roomie had eaten all my steaks! I laughed, 'cause this guy eats nothing but rice & beans. He said he couldn't help it, my meat was so delicious!
He was seriously confused why my meat tasted so good, he like grilled me about it for days after, lol.
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