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It's basically put there to scare people or something, as the transaction goes through just fine every time.
The danger in doing the repeat "glitch" isn't in getting banned.. This has been around since day one, and if Rockstar started to ban people for doing repeats they'd have to ban at least 90% of the player base.
The danger is in getting bad sport points! If you do it too often you can end up being labeled a bad sport, which will prevent you from being able to connect with the vast majority of the GTA online community.
I know of two ways to help counter this...
1. Have whoever you are taking with you commend you during the run. (esc > online > player > their name > commend > helpful) Commending someone for being helpful can help to counter the bad sport points you get from leaving during the cutscene.
2. Do a few missions in between - After 4-5 runs take a break and do a few missions, help someone on a heist, etc. This earns good sport points to counter the bad.