*takes tentative steps into canon-territory* As far as I know Waynecorp has never really been in financial straights, while Stark Enterprises seems to be constantly on an obscene profit/bankruptcy pogo ride, so I'd say Bruce Wayne is consistently richer, but Tony Stark may have greater highs.
If you're talking pure cash reserves, I'd say Bruce. For overall value of possessions, it's Tony (Vibranium suits of armor? ADAMANTIUM armor? Multiple copies of it? Umm... yeah).
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