1. Don't pick a side.
2. Find a few Stormcloak camps and know where the blacksmiths live.
3. Get access to the enchanting table in the Arch Mage suite (preferably by completing the Mage Guild quests, as it's a cheaper faster way to have yourself a storage box).
4. Buy as many iron ingots, leather strips, iron ore and leather as possible. You can use a Tanning rack to make Leather into leather strips and the Whiterun Smithery has a forge to turn ore into ingot.
5. CRAFT IRON DAGGERS LIKE A FOOL.
6. Disenchant everything you can.
7. Enchant all your iron daggers with Damage Stamina/Absorb Health/Banish (eventually - it has the highest value).
8. Sell daggers and buy materials from the blacksmiths and repeat steps 4-7. If you do a run of five-six places at a time, they will sequentially refresh.
9. Rinse and repeat ad infinitum.
10. When your Smithing and Enchanting are done, they aren't. Did you find those Enchanter's Philter's or Blacksmith Elixirs yet? They bump your stats up even higher. And they stack with Smithing enchantments.
11. Use said Blacksmith Elixir, make your spanking new Dragon Armor FLAWLESS Flawless, and your nasty weapon much the same.
12. Double-Enchant everything, preferably after taking some of those Enchanting Philters.
13. Slowly raise your Alchemy so you can make even better potions and really crank out some fantastic shit.
I've heard talk of the Companion's forge really kicking arse, but I've not authenticated that yet.