In this thread, Lorenzo notes that steaks may end up raw in the center if you only leave 'em out for 10-15 minutes to come up to temperature. I recommend 30 mins, but it will probably vary on what room temperature actually is for you.
From Weber's Way To Grill, which recommends salting right when you take them out of the fridge, here's Mr. Purviance's take on why you should consider salting early:
It's true that salt draws moisture toward itself, but over the course of 20 to 30 minutes that's a good thing, because the salt begins to dissolve into that little bit of moisture. When the steak hits the hot grate... [you] create a delicious crust. Any moisture you might lose is well worth the flavor of that crust.
If it's a properly done cheese steak, and it's not sliced in the same direction as the grain of the meat, he's probably right.
It's quite possible that a cheaper cut of meat would have a "beefier" flavor, just because many of the tougher cuts of meat tend to be more flavorful, partially because of the fat content.
All of that being said, it's really a matter of personal preference. Some of of the places near me use the equivalent of "steak-ums" and not everyone's a fan of the texture. If you want to find out if it's worth it for you, get a few friends together, order two subs with the same toppings, one with the upgraded meat, one without, and do a taste test. (and if you can, get one person to order it and label the packages, then hand off to someone else to portion it out, so it's at least closer to double blind, particularly if they use two different labeling schemes)
update : Unlike chicken, beef doesn't have the obvious distinctions between light & dark meat; the normal rule is that the further from the hoof and horn it is, the less that muscle group has worked, and thus the more tender it is ... but as with chicken meat, it's the working muscles that tend to be more flavorful (although tougher cuts). And as with chicken, it's the fattier meat that has more flavor.
Some cuts of beef have the grain run in one direction -- because of this, we can cut the meat across the grain, which tenderizes it. It can be done before cooking, as with philly cheesesteaks, or afterwards, as is done with fajitas. Common cuts used for this sort of treatment are flank steak and skirt steak, which may be difficult to find in all grocery stores as so much seems to be diverted for restaurants.
Besides cutting, other aspects of processing (eg, aging) can affect how 'beefy' the meat is.
Best Answer
Most flavor molecules from marinades don't penetrate much below the surface of the meat. (Salt and to a lesser extent sugar are exceptions: they will gradually work their way in deeper in long marinades.)
Anyhow, if you actually want your marinade flavors to penetrate more than about 1/8" into the meat, the only real option is injection. But if you don't want to do that, poking holes or even gashing the surface with rough knife cuts will help a bit. You can see some photos at this link, showing how a colored dye (whose molecule size is as big as typical flavor molecules) doesn't get below the surface, but gashes and holes can help carry it deeper.
I don't know that there are any real drawbacks to the method, other than having a craggy surface on the meat. As Jolenealaska pointed out in comments, the idea that significant moisture loss occurs from piercing is mostly a myth. (For more detail on that, see Myth 6A here.)