As I've been following various old school blogs, I've read various things that I agree with and don't agree with. In talking with other gamers, quite a few had a negative opinion of the OSR, either from things they've read, or their supposed experiences. I present to you the most common of the negative comments I've heard or read -- most are simply largely untrue. The myths and my take on them:
Old School Myth #1: Rules as Written (RAW)
I've heard this time and again. I've actually experienced it too, when I have to roll a character using the 3d6 method, no assigning of abilities, getting killed just because one dice roll goes wrong (in the GM's hands), etc. Most of these things annoy me, and more often than not is just an example of rigid thinking that doesn't do anyone any good.
But I think that RAW is just a play style. Everyone has rules they like, from random chargen to abstract combat, and that's going to happen. If they didn't like some aspect of the rules, why play? But I don't think it's particularly Old School.
D&D3E has a large number of skills and abilities that you can give your character. In fact, I sort admire it because of that. Properly implemented, this can give you a solid idea of where you came from or who you are. Take Howard's Conan; we know he's from a land of ice and snow, can climb really well because of his upbringing, and also can fight well -- a region where the faint of heart would soon be dead. This could be represented by skill bonuses and bonuses to fight, packaged in a background feat. But, I digress...
D&D3E has a great amount of rules. Rules to see whether you can bluff or intimidate, rules to see whether you can spot something, etc, rules that allow you to do something out of the ordinary in combat. There's nothing wrong with this, per se, but I kinda felt constrained gamemastering. Because I would rather there be a way to solve it without skill rolls, and the designers were intent on simply rolling for everything, it seems. What if I wanted someone to do something to notice something important (like move a cushion, or examine a wall)? What if I would rather they creatively take out their foe, rather than invoking "Improved Crushing Blow" or some such? I felt lost as a player, too.
The rules in Old School games for the most part are frameworks. Each GM seasons his own game to taste. While all GMs, Old School and Modern, do this to some extent, there's some more "on the fly" rulings that must be made. No rules system can encompass everything, and a large part of the OSR loves to tinker with it, at least a bit. If for nothing more than to make sure the next time someone does that, there's not a different set of rules that might hinder the player more or make it too easy.
Old School Myth #2: Starting out as the Little Guy
Another myth is the beginning character as a schmoe. Too often D&D is used as an example, but I can say definitively that every game does not do this. Almost no one can deny that Champions is old (c. 1981), incidentally the same year Tom Moldvay authored his version of Basic D&D. The characters in old-school Champions were hardly average, being superheroes. That also was the theme of Villains & Vigilantes (also '81). 70s-era Traveller was also a game where you were well-trained before you began adventuring. In the Atlantean Trilogy and Palladium Fantasy your character was well-stocked with skills and class abilities, and you were no slouch in Rolemaster, Tunnels and Trolls, The Fantasy Trip, or even RuneQuest. In Gamma World you had powers that set you above the rabble, and in Top Secret you were a secret agent ala James Bond. Need I say more?
For my own part, I consider the "little guy" syndome to be reminiscent of Tolkien, where unassuming hobbits were the saviors of the world. I like the idea of being able to have characters who aren't invincible, but formidable in their own right. John Carter, Conan, Fafhrd, the Grey Mouser, etc.
Old School Myth #3: Characters are akin to Checker Pieces
A comment at Playing D&D With Porn Stars mentions that "The (very) old school treats characters like checker pieces - I don't cry in my beer when I lose a checker piece..." I'm not entirely sure that's the truth. I think it is a bit related to #1. All the rules in the world aren't going to instill a personality in your character, or make a campaign playable.
I've been in those kinds of games -- more power to you if you like that, I'm not particularly amenable to that style. I'd rather have a backstory for my character and have it be a bit more dramatically appropriate when I pass on, thank you very much. It's probably the reason I don't care too much for wargames or FPS games, either. I want to care about what I'm doing.
Now, if you're still trying to wrap your head around all this, or simply do not know what old-school gaming is, pick up Matt Finch's excellent Quick Primer for Old School Gaming. It's free, and chock-full of great advice.