Since then, It's been a lot easier for me to be comfortable with the different ways in which people get their fun, and more skeptical of one-size-fits-all solutions.
This is the unspoken truth, the hidden pillar, the secret door if you will, of the OSR. Not everybody wants the same things from an RPG. This is why you can have fans of 4e and fans of 1e (or even, the gods forfend, fans of both!) enjoying their games in the same room.
This knowledge carries with it some implicit activity on your part. In order to really dig into what it means, you really ought to:
KNOW WHAT YOU LIKE.
This seems stupidly obvious, doesn’t it? Of course you know what you like, right? Who doesn’t?
Lots of people, as it turns out. For something like a decade, I thought the game I wanted was 3e. No more level-limits, lots of skills, feats to make playing the fighter still interesting after level 6, the monsters were as interesting and varied as the PCs, and finally a decent solution to that stupid nonsense about my magic-user not being able to swing a sword.
Only, when I finally got to play 3e, it was unwieldy, overburdened, and just not fun. (Not fun for everyone? Clearly not. But not fun for me. It wasn’t, as it turned out, what I really wanted. It was only what I thought I’d wanted.)
This point has two sides. The first side is, of course, knowing what you really like. This requires a bit of self-reflection, of picking apart what you’re doing and finding out what you do enjoy and what you don’t. The second side is, of course, playing lots of games. The more data points you have, the closer to the truth you can get. And don’t assume that just because one attempt failed that you know all you need to know. You might need to see what an enthusiast can do before you really understand what it is you’re looking at. Oddysey had played and run a few dungeons already before she got to see what they were really about.
UNDERSTAND HOW GAMES WORK.
Once you know what you want, you can go looking for it. But to really understand if a game will deliver, you need to figure out how games work. This may require digging a bit into probabilities, or understanding the relationship between themes and mechanics. It certainly means being able to step back and take that view from 30,000 feet with an objective eye. It’s amazing how many people still think that Old School D&D was primarily about killing things.
While conventional wisdom can be in error, ad copy is almost always wrong. Too many people making games don’t take into account the unintended consequences, the bizarre behavior of players, and the simple truth that things will not be understood, or, at least, won’t be used, the way they were intended. Some simply don’t know games well enough themselves to produce the intended results. None of them know you well enough to match their aims with your preferences.
KNOW YOURSELF, KNOW YOUR GAME.
Once you’ve got those two down, the world of RPGs is your oyster. You can find the games that will give you the maximum fun for the minimum effort. You can houserule “almost” games into near-perfect matches while avoiding the trap of feature-creep, or breaking things with unintended consequences.
And, when someone asks you for advice on games or your write a review, you can honestly speak about who the game does serve, and who it doesn’t serve. You can get beyond the edition wars to find the hidden gems in the most “unplayable” systems. You can not sound like an opinionated twit spamming your knee-jerk preferences and stereotypes, and start sounding like someone who really knows and understands games, and who wants to be honestly helpful instead of a cheerleader for their game de jour.