If GTA V game rules are to be followed to a tee, there's one rule that makes this extremely tedious, if not impossible. • Any strat that requires an active internet connection is banned. This includes but is not limited to: Using the Rockstar companion 'Ifruit app' on your real life smart device to affect your gameplay(even if just visually), trying to enter and exit the rockstar editor to force a random switch. 3 of the 6 stocks require use of the BAWSAQ stock market, which cannot be accessed without an internet connection. Whether BAWSAQ stocks are allowed is up to the category extension moderators for this, but I highly doubt any category like this would ever be run without significantly decreasing the required money.
I've considered doing a run like this for awhile, so it's cool that I'm not the only one who's interested. Good luck to anyone who tries to run this.