I was just thinking of ways to mend this time-consuming problem. I thought about just selling the money and pocketing the caps, but I'd lose a great deal of money in the process. One possible solution would be to have an NCR official that exchanges different denominations for bigger bills. For instance a man in the NCR embassy on the New Vegas Strip that will exchange all $5 or $20 bills for $100 bills. This would significantly reduce the time it takes to exchange NCR cash for chips. Not only that, but it would give a good target for Legion or thief/stealth oriented players to hit for cash (albeit this would be a risky move).
Just a thought. Any other ideas?