Quote Originally Posted by Zeful View Post
I want to give D&D another shot, it's why I'm here. But for me 3.5 is almost totally ruined as a system, and playing it would require far more work and interpersonal dependence than I'm capable of.
I think you're pretty much trapped in an unwinnable situation. D&D, due to its nature as a rules-heavy gaming system, is naturally going to allow players to "optimize" if they choose to do so. Even 4e, which for all practical purposes narrowed the gap between RAW "low op" and "high op" significantly is still a game where optimization happens (and some would argue, is baked into the system, to a degree that didn't even exist in 3.5). We haven't seen too much of 5e, but I am confident that whatever gets released will be picked apart on the internet (just like 3.5 and 4e were), from which practical optimization will follow.

What I find more unnerving however, is your general response to "optimization" (and let's be clear that optimization is not always clear cut. One man's optimization, is another man's "in character choice"). You can't be afraid of it. If you worry about optimization, you're going to be spending so much of your time focusing on how to "beat" the optimization, rather than doing all the stuff that makes being a DM enjoyable.

What Pair o' Dice said worth repeating:

1) One of the most important rules for being a player: "Don't be a ****". A player that brings a Cleric 1, switches into Psychic Warrior at level 2, and then goes straight Crusader at level 3, should know better than to pick up a 1d2 weapon once they start nearing level 11. At the same time, "don't be a ****" != "don't optimize, ever". Some players will naturally see that Grease is a superior spell than Magic Missile, and that Power Attack and Improved Initiative are better feats than Endurance and Run.

The dividing line (I think) between "being a ****" and "not" speaks to Pair o' Dice's second point:

2) "Be honest about what you're trying to build". I tell my players straight up in our 4e game: I expect you to optimize, but don't bring a Ranger with dual frost weapons and a bevy of feats to add to cold damage you deal and tell me your character "is not optimized". Get in the habit of asking about what direction they want to "build" their character to, and why they choose particular feats or spells. You'll not only learn why they're creating the character they are, but also you'll be learning more about the game AND how your player approaches it.