Because I like talking about my characters, here’s how they compare on a scale of wealth and how honestly they acquired that wealth...
Gaila: is absolutely loaded by Tamrielic standards. Part of it comes from her day job as an alchemist, but most of it comes from heists. She doesn’t participate as much in petty theft, but prefers to steal the stuff that is bolted down - more interesting that way. Gaila steals for the challenge, and is very free with sharing it out again.
Ashrarz: confirmed hoarder of certain items. Regularly tangles with dragons, and keeps their bones, and Lydia has to help him cart all that back to Whiterun.
Meya: some of Meya’s money comes from contracts she’s completed with the Companions. She scarcely touches it, and doesn’t know how much she has. She also has various entitlements in the various Holds she’s saved, including a whole house in Windhelm, and a housecarl that she’s never met.
Veren: owns a surprising amount of land that he has rented to generations of Nords. His fortune is officially held in Falkreath Hold, and Jarl Siddgeir was very rudely surprised when Veren showed up to dispute the young ruler's attempt to requisition it. Veren goes way back with all the old families in Falkreath, and is particularly respected for closing the four Oblivion gates that opened there during the Oblivion Crisis.
Isayne: all of her money is tied up in magic; enchanted artifacts, spell tomes, staves, and soul gems. She doesn’t have a house, but instead leaves the bulk of her material possessions in the hands of a bound Dremora that she calls Gerard.
Orn: doesn’t consider his clothing to be owned, merely borrowed for the sake of propriety. But in terms of perception of wealth, Orn is richer than kings, enjoying the gifts of the sky, the wind, breath, and life.