That is certainly a strategy especially if you only have 1 BB/Serve account and it works for you in terms of comfort level. You would just have to make 5 separate transactions. However for people with multiple BB/Serve accounts this doesn't work as well since you have to make too many trips to CVS and not to mention showing 10-20 CVS transactions of the same amount.

Keep in mind you can still find other ways to dump OVs such as AP. Its not like you are totally boned. But I agree in general, it is not good strategy to bite more than you can chew if you can't find a good way to dump them all in a relatively short period of time.

But for me I have 2 BB/Serve cards and just 2 days ago I bought $5K in OVs around 7 PM. Around 8 PM dumped $2K at Wally and then waited until past 9 PM for the next day to roll around and around 10 PM, dumped another $2K at Wally. So I was able to dump $4K in about 3 hours. Then the next night I waited until past 9 PM and dumped my last $1K at Wally onto one of my BB/Serve accounts. I was able to dump $5K in OVs in a little over 24 hours.