Sucks. But I don't think there's any easy/systematic way to cure that. Needing a high-caliber DM is a requirement for D&D.
Um, needing a high caliber DM is NOT a systemic fix. A systemic fix would be something that did not require a high caliber DM, because it was fixed by the system.
For those of us who picked up the game in the early days, having a high caliber DM was not an option; our DMs tended to be whoever had the inclination to teach themselves and enough money to pick up a DMG.
If D&D is feeling repetitive, perhaps your DM is not doing enough to vary the environment. Like the pirate vs. the foot-soldier example, circumstances should change enough that different strategies are optimal at different times (i.e. what happens at character "build" can never be optimal and is of little importance). Tonal shifts in mood and situational mini-games help keep things fresh. (Through the Looking Glass, on Mars, swimming through underwater mazes, hacking through jungles, mass combat, court intrigue, switching bodies, etc.). That way, you get to wear many hats irrespective of class ("when in Rome..." again).
You can vary the environment as much as you want, but at some point changing "the environment" ends up being more like choosing a different background when playing Streetfighter II. I just found the combat a bit dull because it was static. I acknowledge that there is a tactical game to be played with 1e initiative rules, but it is very much a dissociated, metagame challenge, whereas I prefer combat decisions that operate for the characters similarly to how they operate for the players.
It isn't the superhero stuff that attracts me to 4e. For "martial", or nonmagical classes, it is the more mundane stuff.
Take a plain 4e fighter. To start with, when he attacks an opponent he can "mark" them, basically focusing attention on the opponent and forcing the opponent to pay attention to him. When it is the opponent's turn to attack, he can attack the fighter, but the fighter usually has a high AC. He can turn to attack someone else, but if he takes his eye of the fighter to do so, the fighter will punish him by taking a swing at him; and because the enemy knows about this risk he is nervous and suffers an attack penalty if he attacks the fighter's ally. So the enemy has a choice; he can attack the fighter, who has a high AC and high HP; or he can attack someone else with lower AC and lower HP at a penalty, risking damage to himself. So there is a ton going on with that single mechanic.
The fighter also gets two other "at-will" attacks at first level. Let's say one of them is "Tide of Iron". All that lets him do is use his shield to shove the enemy back, and move into his space. Another might be "Knockdown Assault", where you give up doing weapon damage in order to knock the enemy on his ass. You would use these in different situations, and they aren't always all that useful, so sometimes you fall back on just whacking our opponent and doing damage. But when they are useful they can change the relative positions of the combatants, or place one at a significant disadvantage.
I first level fighter get one ability which he can use once per combat. Let's say you learn "Shield Riposte". If an enemy who is standing next to you attacks you or an ally, and you are using a shield, you can attack the enemy and push him back; and while he is off balance you have a limited ability to reposition yourself.
You also get one maneuver which you can use once per day. I have issues with daily powers for martial characters conceptually, but the point here is whether they are superheroic. Let's look at "Driving Attack": once per day you can attack the enemy, and if the attack hits, push him back and set him up for a second attack by you; if the second attack hits you push him back again.
In a game where it is very important to keep enemy fighters away from your squishy spellcasters, holding your own line, or breaking the enemy line, has real consequences. Jockeying for position can be very important, and these maneuvers that break lines (and other maneuvers that hold them) are very important. And they are just one way that quite mundane maneuvers can be tactically significant. I really enjoy this, which is a bit reason why 4e is a better fit for me than 1e.
To put it a delicately as possible, to mechanize "fighting techniques" is wanting to start out with special abilities. As a DM, I make it possible to acquire special abilities---but you have to earn them...like a magic-user finding a new spell on a scroll, or a cleric a magic mace. Baking them in at start-up is just a small bit of wish fulfillment.
This is exactly how I run my 4e game, even though it is "mechanized". For the most part, as a nonmagical PC your abilities are pretty mundane at the start; you have to earn (and learn through training) the really cool moves. Let's say our fighter wants to specialize in polearms. Polearms are good for pushing enemies and knocking them down, if you learn the trick. But first you have to learn maneuvers that let you push your opponent while you are not using a shield - Tide of Iron won't cut it. So you have to learn a few more difficult maneuvers to make it worth your while, say two or three maneuvers that include a small push. And then you can learn a technique called "Spear Push", which lets you push just a little further with those maneuvers as log as you are using a spear or a polearm. And then you can learn a technique called "Polearm Momentum", which lets you knock enemies on their ass as long as you are able to get that bigger push on them.
So in order to reliably knock enemies down, you need to have heavily invested in specialized training. You need to have found someone to teach you, and learned, two or three maneuvers with a "push" attached to them; learned a technique to extend that push, and learned a technique to knock down enemies you push. The earliest this can be achieved is generally 12th level (11th level if you find certain magic items). Oh, and you can only learn these techniques if you have a high dex AND a high wisdom.
Again, I know this isn't for everyone, and I'm not trashing the early editions. I'm just saying the early editions don't have this, and it's something I want.
To respond to a couple of posts by
@TerribleSorcery and
@EOTB that were posted after I started writing this, I looked at 4e options for gladiators and "pirates". Basically, 4e gladiator skills tend to be focused on individual ability; he relies less on the other party members, and he is less oriented toward supporting other party members. So a gladiator will be more effective in a one-on-one fight than a normal fighter, and arguably less effective when working as part of a team.
EDIT: Arena fighters also are skilled with improvised weapons, and get +1 AC if not in heavy armor, which is NOT equivalent to wearing heavy armor even if you have a high dex.
Mariner options tend to focus on giving the character skills related to operating on a ship - out of combat skills, moving in rigging, navigation, balance, additional languages - at the expense of combat ability.
