I'm almost 100 hours into the game and I think I'm around level 40 something, and I've never had the feeling that I'm rich, and I even steal every last coin I can pickpocket off of every person I see. I don't even pay for training of my skills, I hand over the money for training, pickpocket it back and then hand it to them again to train again, and pickpocket to finish.
I even sell 95% or more of all that I carry from looting enemies. What I'm getting at is that I've never broken 20,000 gold held at one time. If I did, I would pay that 20,000 gold bounty on my head in Markarth. I've sold everything I've felt I can sell and buy all that I need or feel I need, and I haven't felt that I was rich. I've even become a near master blacksmith and I'm still not making enough money to keep up with my purchases.
So, I guess it is a matter of how you play that determines how long it takes to be rich and stay rich.
Zhukov said:
The most fun I had with Skyrim was in the first 5 hours or so immediately after the game removed the training wheels and set me loose on the world.
What are these training wheels you speak of? Because after I escaped the dragon attack in the beginning, I followed what's his face (don't remember his name) to Riverwood and met his friends and whatnot, he said he would go on ahead somewhere, and I said, "Okay you do that, while I go off and play the game, explore, and whatnot." That only took like 40 or so minutes tops.
Heck, I think I was at least 60 or more hours in before I even set one foot on the steps to High Hrothgar to meet the Greybeards.
As I've said, I'm only almost 100 hours in, though I've been taking a break, and the last actually main storyline quest that I did was where I witnessed for the first time, that one dragon resurrecting another. It's something like only the 7th or 8th main quest. So, in that almost 100 hours, I've barely touched the main story, I haven't even picked a side yet.
Though at last count, I've only killed like 17 dragons.