If you are okay submitting the high dollar card at $499 for insurance purposes do it. They won't balk at it. I submitted a card at $499 that was a total POP 2 for all grades, and both had sold for more than $2k and it went through without a hitch.
I don't know if they will do live grading at the show you mentioned, but double check the terms of the voucher. If I remember correctly, it would not be valid on on-site grading at shows as they charge a premium for that.
Card Saver I semi-rigids is how they want the cards sent. Penny saver soft sleeves up to you.
Good luck!
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