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>I could just imagine, blowing the dust off my laptop and logging into my Schwab account...

Does your fantasy include the website telling you your browser is unsupported followed by several hours of installing updates?

You mean the world isn't still using firefox 3.6 on ubuntu 12.04?

Well, some of it is

Wow, parts of the "how the character became a millionaire" montage that never leave the cutting room floor.

It could actually become a good premise. An ex criminal with a lot of money but those properties are completely unrelated to each other.

Explain to the probation officer why they're searching for luxury homes while sleeping on their brother's couch

Coming to the realization that it was the act of doing absolutely nothing that made them rich.

I bet it's happened before.