Odd question about mail in the U.S. (Including an envelope in an envelope)

[Mystic Muse]

Okay, basically, my question is this. Is it possible for me to go to the post office, pay for an envelope to send to someone with insurance, and then pay for another one for them to send back with insurance?

I'm a Magic: the Gathering player, and I'm trying to get all the cards in my main deck signed (When the artists are actually WILLING to sign. >.>;). Due to the rather high cost of the cards though, I would be very, VERY irate if they got lost in the mail, and artists are practically never willing to actually go to the post office to return your cards. As a result, I was planning on getting an envelope that could just be sent back, insured for the amount the cards are worth.

Is this something I can actually do? I would go to the Post Office and ask, but I won't have the time tomorrow, assuming they would even be open.

[Bulldog Psion]

I'm not 100% sure if this is the case, but it sounds doable. When I worked at the Post Office a few years back, I never had a case exactly like that, but it sounds like something potentially feasible.

If I remember, I'll call someone I know at the Post Office in town here in a few hours, and see whether they know for certain whether it can be done.

An alternative, of course, is just to find out how much the insurance costs and stick in a bit of money to allow your friend/contact to buy the insurance for you. That, of course, depends on how much you trust your contact; but if you're sending them a high-monetary-value deck full of rare cards, you must repose some faith in their honesty.

EDITED WITH UPDATE:

I called and they had such a hard time understanding what I was after, that I'm leaning towards the "enclose some money" part just to spare yourself the headache. I'll try calling someone else shortly, though.

[Grinner]

I recall hearing instructions years ago about including a self-addressed, stamped envelope for participation in some promotion, so I can't imagine that would be an issue. The only problem is how one would go about insuring both...It's not like it sounds difficult, but the way insurance works complicates things...

[Mystic Muse]

Yeah. It's not that I don't trust the guy, it's that I've never emailed an artist who is willing to go to the post office.

[Alent]

If talking to one of the clerks is unproductive, maybe you could insure the mail and envelope with one of the new(ish) self-service postal machines that the USPS has in the post offices now?

You can insure a piece of mail with one of those, as I recall. It shouldn't be that hard to label two at once. You might need to ask an employee if there'd be any difficulties with the insurance if one of the labels is postmarked by another post office.

[tomandtish]

While you technically can try to do what you are suggesting, it's best to send the person mailing you the cards the money and have them do it. Why?

Insured mail comes with a receipt, including date of print. One thing that can cause problems is if the date of receipt doesn't match the actual shipping date.

So if you insure your return envelope on 5/1/15, and the other person doesn't even ship it until 5/5/15, you could run into issues if they start wondering why the delay. That is, according to the insurance you shipped this on 5/1.

Even if the Post Office itself can post-date the insurance (and you'd have to , you and the person shipping you the cards would still have to make sure it matched up.

Incidentally, note that one thing you can not insure is a standard envelope or flat (http://pe.usps.com/text/dmm300/503.htm#1063640). Looks like you need the equivelent of at least a priority envelope, so there are those extra charges anyway.

All things considered, yeah it's best if the seller does this on their end.

[Bulldog Psion]

Just as a side note, priority mail automatically comes with $50 worth of insurance. I know that probably isn't applicable, but I thought I'd mention it here.