Solitude when my character starts ballin with gold.

Falkreath, I live there.

Whiterun, because it's in the center of the map and has things that I need.

I would figure it would be Whiterun here for most people

From a Roleplaying prospective... it is the center of the map and always have a bed and some food. Even when I own a home elsewhere, I spend way more time in Whiterun then next, the Rift or Windhelm since I seem to do all the quests on that side of the map.

Whiterun entirely because of its strategic location. Next is Riften which has the most merchants in the cities. Then is Falkreath where I go often because I use Lakeview manor, though I never stay in Falk for more than two or three minutes.

Yeah but the guards are just as stupid everywhere else.

"Got to thinking maybe I'm the dragonborn..."

You're saying that TO THE [censored] DRAGONBORN MORON!

Whiterun for me, due to it's convenient location and layout.

Second place would go to Riften.

Riften.

I need to keep order in the Thieves Guild since my character is the guild master.

Whiterun for me, just because my home and stuff is there and its location, riften is second with the theieves guild being there.