What if someone has been betting frequently, but they've been winning so far? They'll be deemed "addicted" by this algorithm. Should they be?
How much will it cost to administer this program?
How confident are you that it will improve outcomes?
Why should I be required to share details of my finances in order to play?
Legal gambling has issues but I would definitely vote against your proposal. Keep regulations simple, either allow the activity or don't.
It's not worthwhile to try to duct tape over side effects with mitigation programs of questionable impact that will inevitably be expensive to administer, all while arbitrarily invading peoples' privacy.
First of all it's not my proposal, but the proposal was simple enough and could improve outcomes.
None of these edge cases are actually issues if the system is "gambler A talks to official B before they're allowed to place more bets."
If this was an automated system sure these are issues to sort out. If it's just "talk to an official who confirms you know you're addicted to gambling and provides links to support info" before your next bet is allowed to be placed, none of these edge cases matter.
Those who have the wealth that or are not actually addicted can just ignore what the official says. No need to verify wealth, no need to check if they're winning or not. Just "hey you're placing bets at frequency X, are you sure you're not addicted? There is help available, here's some links to support materials."
Then that very wealthy person talks to an official who verifies they can afford to bet that much.