One thing that PSA will require is a separate order form per service level. So if you join the club, you would have to use all of the voucher on one order form. The voucher is good for 10 day service level and cards valued to $499.
Then if you submit the $500 and up valued card that would have to go under (Express Service - 5 day level) it would have to be on a separate order form and yes you will pay shipping twice.
However you can ship them out to PSA in one box, notating the Express Service level on the box and PSA will accept that. And normally get both orders out pretty quick...
If you put the voucher and value the $500 card at $500 and over on one order they will hold up the order until they reach you and get the ok to split them into two orders...or you can send the $500 card in as part of the collectors club voucher and value it below $499 and should be ok..
Either way will work the valuation is really for shipping insurance purposes and to designate service level on really expensive cards...
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