Extensive spoilers follow, so please don't read farther if you don't want to read about things that happen in game.
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Still here? I'm planning for a Legendary Dead is Dead character after trying a few hours of Legendary difficulty. I haven't played through the entire game even on Adept. (I find on Adept, I just don't get into any serious danger, so I keep amping up difficulty and restarting.) As for what "Dead is Dead" means, it's no reloading saves; if the character dies from a fall or a sabre cat attack from the rear, just dead. So I want to plan as much as I can, because I don't want to have to restart after a surprise death a hundred hours in.
This isn't a thread to say "oh look how clever I am"; I know there's a lot about the game I don't know. I've read guides, but patches (official ones, I don't play modded) change gameplay to the point that certain things like the Fortify Alchemy enchanted gear / Fortify Restoration alchemy loop don't work to the extent that some guides state they do, &c. This is more a "this is what I think might work, comments & feedback welcomed" thread.
I'm prioritizing survivability to begin with, though balancing gold income, collecting items (I'm a collector), and long-term power are also considerations. All the points for the first ten levels minimum go into Health.
The game plan -
Female Breton uses heavy armor and shield, but picks up Novice Hood, Novice Robes in Helgen, activates Thief stone, picks up Faendal in Riverwood (he carries stuff and tanks), activates Golden Claw at general merchant, talk to innkeeper to find out what jobs are out there (hopefully a bounty at Halted Stream Camp, which comes into play later), buys iron ore and sells extra weapons and armor (but keeps equipped stuff and daggers), buys petty soul gems (especially empty petty soul gems) a few lesser soul gems, and alchemical ingredients costing 5 gold or less, sleeps 1 hour for Well Rested, mixes potions and sells to general store. (Why not Lord stone or Shadow stone? Because I don't think I need them at this point.)
On the way to Whiterun, stop by Honeymeade's external barrels to pick up the high value per weight stuff, pick up vegetables and stuff, look for an encounter with the Companions and a Giant, equip heavy armor in case of surprise wolf attacks.
Gets to Whiterun, picks up more iron ore and petty soul gems (especially looking outside the city for the Khajit cat-people caravan), talks to the woman outside Warmaiden's to get a sword to give to the steward, finishes off for a total of four empty lesser gems, books of Soul Trap and Summon Flame Atronach, loots Jorrvasker (sp?) and palace for soul gems. Does the quest with Carlotta and Mikael for gold if they're at the inn which I go to to sleep 1 hour, mix potions and sell to alchemist. Make potato soup and vegetable soup to eat later, sell excess food to innkeeper.
I found putting off Bleak Falls Barrow and leveling a bit got me a Frost Troll in a snowy part of Bleak Falls Barrow. Easy enough to beat with a fire enchanted weapon, but that's expensive, and I want gold to go for a house in Whiterun ASAP. So I hit Bleak Falls Barrow early so I won't see a Frost Troll. Before actually going, though, I activate Warrior Stone, then go to Riverwood, steal iron and steel, forge and/or upgrade steel armor. (I need to be at least level 2 and have a perk point to spend on Steel Smithing; if I figured I'd be level 3 at this point and have a perk point to spare the other point went into Alchemy). Why wait so long, because maybe I pick up Steel Armor when speaking with the Jarl.
Most walking around is done in Heavy Armor (in case of surprise wolf attacks), but switch to Novice Hood and Novice Robes just outside Bleak Falls Barrow, summon Flame Atronach, and use bow to attack. Hide behind Faendal. Inside Bleak Falls Barrow, same routine for the rest of the bandits just inside, then switch to Soul Trap (still using Hood and Robes) for skeevers, then Soul Trap with heavy armor against spider miniboss. Hiding behind Faendal all day. Then for the draugr section some mix of bow sneak attack and Flames (just shot into the air with no target) to bait draugr out one at a time so they can be relatively safely Soul Trapped. If draugr start coming at me, run around and switch to heavy armor and healing as a last resort.
I had a lot of problems with blade traps on previous run throughs, but I think a mixture of walking and heavy armor and shield and healing ought to keep me *relatively* safe, plus telling Faendal to wait a couple rooms or some distance away so he doesn't run through the blades to attack draugr on the other side.
Boss with bow kiting and emergency heavy armor/shield switching plus jumping around a lot (he likes to run around the pedestal where he spawns), finish up with a Soul Trap. Exit dungeon, walk to Mage Stone, activate it. By now I easily have enough levels for a bunch of perk points; boost Smithing, Alchemy, and Enchantment as high as they can get, Heavy Armor and Block, save a few perk points as smithing, alchemy, and enchantment are all going to increase soon. Walk to Riverwood, complete Golden Claw quest, buy more iron ore and petty soul gems and empty lesser gems, sell off minor armor pieces for weight, , walk to Whiterun, check for Khajit caravan, buy more iron ore and soul gems, make sure I have loads of arrows, wait until it's maybe 4 AM, then start the dragon thing. I wait until 4 AM so it'll be early morning when fighting the dragon; it's a long fight and I want good visibility.
Top of tower and shoot arrows at dragon; if dragon looks like it's getting interested in me, run down stairs and hide. Repeat until dragon dead (easy peasy), return to Dragonsreach, pick up Axe of Whiterun (hopefully drain stamina, a relatively expensive weapon enchantment). Talk to Farengar to start quest to deliver frost salts to alchemist, deliver them and loot the alchemist, talk to the innkeeper for jobs, sleep 1 hour at the inn, return to Dragonsreach to disenchant Axe of Whiterun and the weapon of cold from the boss in Bleak Falls Barrow, then enchant the 30 or whatever weapons, talk to the steward for jobs. Sell the enchanted weapons at the Skyforge, at the Drunken Huntsman, and at Warmaiden's, and pick up more ore and petty gems, look for a Redguard arguing with wife and start up the sword-hunting quest, go to Companions and start admission first quest. Sleep 1 hour, mix potions and sell to alchemist, return to Dragonsreach and buy house with additions (easily enough gold), strip Faendal and dismiss him, equip the new housecarl follower, go to inn and adopt Lydia, buy all the steel bars and ebony ingots and quicksilver available if any, return to the house and unload iron ore and leftover ingredients and whatever else.
Hopefully one of the missions (bounty from inn or steward, Redguard's sword-hunting quest, or Companion quest) requires going to Halted Stream Camp, because I need to go there anyway to get a spell to transmute all that iron ore into gold. Even if no mission requires it, go to Halted Stream Camp anyways, do the things, sell the stuff, save two mammoth tusks (one woman in Whiterun wants one, and someone in Riften wants one, and Riften's the next stop after this). Novice Hood / Novice Robes and summon Flame Atronach, then switch to Heavy Armor for the fighting. After cleaning up, transmute iron ore to gold while walking to the Warrior stone, activate it, then go around Riverwood and Whiterun buying up iron ore and petty soul gems, stealing gold, hides, ingots, alchemical ingredients, and generally high-value stuff, interspersing with more Transmutation spells until finally running out of iron ore. Transmute all the gold ore into gold ingots at Warmaiden's in Whiterun, sleep 1 hour, forge a load of gold rings, sell them off to the mage at Dragonsreach and the general store. Start the light armor track with Elven Armor for Smithing (continuing to Advanced then Glass then Dragonbone later). With all the gold, try to find a weapon with flame enchantment or soul bind (maybe both), continue to stockpile steel ingots. Return to the Thief Stone, then walk to Riften.
Generally at this point the concentration is on picking up petty soul gems filled or empty, empty lesser soul gems, and a few empty common, maybe a couple empty greater and an empty grand soul gem, iron ore, and steel ingots, plus cheap alchemical ingredients. Particularly also looking for gear to boost enchantment, alchemy, smithing, heavy armor, magic resistance, and fire damage and soul trap weapons. Stuff to steal (I know stealing is wrong, but it's the game) include hides, ingredients, high-value items for weight (like fine clothes often at 35-40 gold per pound), ingots, soul gems, any items with enchantments not learned yet. (Ingots, soul gems, and ingredients get used up or changed into other things when crafting so don't have the "stolen" tag).
Before entering Riften, look for the shrine to the northeast for the amulet for better prices, then join the Thieves Guild in Riften and unload all stolen items. Do the "Book of Love" quest for the temple of Mara in Riften for the 15% magic resistance bonus, the "Unfathomable Depths" quest for the smithing bonus.
Then it's off to Markarth to do Agent of Dibella, on the way look for magic resistance boosting equipment or any other enchanted equipment, work on boosting smithing (along the light armor path), alchemy, enchantment, heavy armor, block, conjuration along the dead thrall path, restoration (which helps with dead thralls eventually), destruction (which also helps fire/frost/shock enchanted weapon damage) and archery. The light armor Smithing route has some heavy armor along the way (Carved Nordic armor, and Dragonbone at the end). The goal is to get Smithing to 100 and Heavy Armor to 100, then reset Heavy Armor to 15 and go along the Light Armor path. It's done this way because Heavy Armor really helps that early game survivability, and by the time Smithing gets really high, Light Armor is better than Heavy Armor in many ways (but smithing has to be REALLY high).
All this is leading up to the Black Star quest. After that, progression goes on whatever other things.