The problem on this kind of terms was sometimes casino is using it to get more time to find a violation on the account in case they see that the account keeps winning. Like what happened to his case which casino just process his withdrawal because there’s nothing to find on his case rather than his betting history that keeps on winning.
Does casino typically flag a user account if they saw them that always win and bet on sports that is not popular?
I'm not entirely sure this is what happened here. From what I can tell, the user didn't had their details filled in and probably triggered a KYC matrix during its first withdrawal. If you register just with a nickname on a regulated casino you'll always be triggered on the first withdrawal. We don't know the full story here. Look what they wrote:
Hello again,
As I got informed Jackbit team has requested verification and after that you will get your funds right away
Thank you
So I'm 100% sure that we don't know exactly what happened, OP could maybe point out the exact process which happened, but from what I can tell (and I'm purely guessing here) is that he registered, didn't fill out his details properly, deposited $500 which was the first flag, won, and then immediately cashed out. Since this is a common abuser scheme he got flagged, and maybe he got flagged with 100 other users, so the ticket was pending. Once he reported it here, the ticket got bumped. He then filled out his details and withdrew his winnings.
This is my guess because it happens more than you think, but I would be happy if OP tells the full story.
Does casino typically flag a user account if they saw them that always win and bet on sports that is not popular?
From my own experience I can tell you that no one wants to build their reputation on broken deals, a licensed and regulated casino pays out the winnings regularly if they are within the payout limits. If it's above the payout limit (e.g. $30.000 or something, depending on their TOS) then they pay it out on a monthly basis. The thing is, payouts don't happen that often (the house mostly wins) but when they do, it's in an operators best interest to pay it out. If you don't do it, 1 year from now you can close down the business since you'll be losing the license, the game providers and payment providers.
One user before me mentioned how he reported them to AskGamblers, and this is what happens often. If you create issues for the users, they complain to your business partners, and if the business partners see that you're a scam, no one will want to offer their services to you, so basically you can lock up the operation.
Because of that, it's in everyone's best interest to pay out the winnings *if* everything is legal and within the TOS.
But that aside, I do encourage everyone to report scammy operator behavior, and I do agree that six months is too much for the investigation. Usually this can be done within 60 days without any issues if there's enough man power in the team, but if it's a new casino with just a handful of people, then it might take a month longer, but six is too much.