Excluding the Hold Capitals, what town/settlement/stronghold do you think is ether the largest, most powerful or most important? Before the dragon wrecked Helgen it looked pretty big but it didn't seem to have much in the way of commerce and I know none of the strong holds are big but they kind of have the best mines on lock. Anyway what do you guys think?
Hmm, Dragon Bridge is, from a tactical standpoint, the most important town. If you take Dragon Bridge, you can create a choke hold for anyone coming to invade Solitude by the roads, or you can seige the city by cutting off supplies. Nevertheless, whoever owns Dragon Bridge owns the road to Solitude.
But economically, I'd have to say Rorikstead. It's a relatively large farmland with plenty of room to grow. It sits on a main road to Solitude, Morthal, and Markarth, two of which are very wealthy and powerful cities. It's also on the western "gate" to the north of Skyrim, so it's likely to see a lot of traffic.
Traveling to High Hrothgar requires taking the 7,000 steps, beginning in Ivarstead.
I'm guessing the 7000 steps is symbolic and holds some deeper meaning in the lore. If you take the backdoor up the mountain, you'll be skipping out on the initiation and that probably wouldn't be what the Greybeards would want.