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Perkless is right. What I said above is just how i play and was to give you ideas on how some other people do it. The beauty of this game is you get to run around and do whatever you want.
An exploit can be used to acquire a house without losing gold; requires possession of the amount of septims needed to buy the house. Immediately after telling the Steward, I'll take it!, exit the conversation before he finishes talking, store all your gold in any nearby chest, and the money will...
Here is a link on how to become thane of each hold. If the objectives don't include requiring property then your probably good. http://elderscrolls.wikia.com/wiki/Becoming_Thane
I chose dragonplate armor because I thought that since I was dragonborn what better then to wear their bone to protect me from their bite. I also wanted lighter armor opposed to heavier because I seem to be over the weight limit a lot, any small bit of weight reduction helps.
I personally enjoyed the dark brotherhood quest line the most because it had a lot of twists and it kept me interested. I think think that you should do whatever your character revolves around for example if you have a warrior type character do the companions first, assassin = dark brotherhood...
Completing the dark brotherhood quest line gives you the opportunity to get a lot of money. The night mother gives you quests to kill someone and you get 1000 gold each kill. For legal money you just have to go through dungeons and the like for loot to sell. Most fast easy money is gained illegally.
Choose the ancient shrouded mostly because the nightingale hood really does nothing for you. The ancient armor provides better enchantments for assasins, although nightingale looks way cooler.