I'm Planning on starting a Legendary DiD for the first time. I've done DiD before just not on Legendary, so has anyone got any advice on how not to get my [censored] handed to me in the first 5 minutes?

Sneak! Best armor you can make/get you hands on, every level up into health, magic resistant items are pure gold, and the lord stone.

Using the lord stone is good advice as you will need a way to mitigate some incoming damage. Stealth is not a necessity depending on how you've built your character. You can go toe to toe with people and still dominate with 2h weapons, dual wield, or sword n board as long as you have some dodging/bashing skills. If you do choose a class that uses melee damage, be very careful of enemies that can kill cam you easily(bandit chief with 2h weapons, dragons, random road encounters with 2h weapons). If you put all your level ups into health you can reduce the chances of ridiculous kill cams(though I'd still heal pretty quickly if you take a hit from the enemies mentioned above).

Even the intro can be a bit difficult, but try to let either Hadvar or Ralof take some of the heat from you, unless you think your dodging skills are already top notch

Not sure if you are set on a particular type of character but utilizing Conjuration and Illusion is arguably the most powerful combination in the game. Very effective, as you spend your time avoiding direct combat. Thus, you are virtually avoiding damage for 95% of all encounters.

Then there is the Stealth element that is quite powerful in itself. Joined with Illusion, it to is quite valuable. The downside, compared to the Conj / Ill duo is you need to ensure you can deal enough damage for a given enemy. Be that backstabs or confronting the last enemy of a dungeon. Conj / Ill is just as effective on Legendary as it is on Novice.

Playing DiD on Legendary seems to me a bit like repeatedly playing Russian Roulette. It's not a question of if you will die, but when.

I have 2 characters still standing, and don't think they'll be KO'd at this point unless I fall off of a mountain. This is without companions or summons, just straight fighting with a melee weapon(no potions either, just restoration....aka no insta heal spam). Float like a butterfly, sting like a bee

I'm working my way up on the difficulty, starting off on the normal setting. As i feel more and more comfortable i bump it up a notch. Then as i begin to feel more comfortable i'll bump it up again. That's what im doing right now. It's my first DiD character, and its helping me get the feel of the type of gameplay i'll need to use once i make it to legendary.

Fight smarter, not harder.

Early on, use a shield often. It'll be the one piece of armor that will save you more than anything else.

Don't be afraid to run from a battle. One or two enemies is one thing, but more than that, and you'll be spamming potions.

Speaking of which: drop loot for potions, especially around level 10, when enemy levels change. It's a big jump, so being unprepared can easily see your character's name on a tombstone.

I don't recommend followers with Legendary DiD until later in the game. They're so ridiculously prone to giving away any advantage you may have in a fight.

Sneak is a good skill to boost, but this won't work well without a good distant weapon, early. This is because you won't have enough experience to sneak well enough to stay hidden and your dagger won't be much help to you.

Legendary can be... difficult at times, but run whenever you can.

Finally, don't take on the troll to High Hrothgar on your way to meet the Greybeards. It'll eat you.

Unless you have quick reflexes, of course. Then you can just laugh dancing circles around him and pounding his head in(which will take forver at a low level but is funny anyway)

Yeah, but who wants to spend nearly 30 minutes trying to kill it? Okay, I admit I did, but I won't do it again. I'd rather just run around it and deal with it another time.

Oh, yeah, one more piece of advice: buy a horse! When traveling, this will help make it easier to get away from things that want to eat you, like those nice kitties with the big teefies.

That's great advice. I would probably try to avoid sabre cats and bears early on. Their attacks are really annoying to dodge, and bears have a ton of health. I definitely would not be trying bears with a melee character under level 20