Complicated mailing/SASE problem

I’m trying to send a weighty-ish package (just under 2 lbs; will fit into one of those Tyvek Priority Mail envelopes) to 2 people in succession. I don’t want the recipients to have to do much more than seal an envelope and drop it in the mail.

Recipient 1 needs to sign stuff and then send the package on to Recipient 2.

Recipient 2 needs to sign stuff and then send the package full circle to me.

I had thought it would be easy enough to simply buy the appropriate postage, stick the proper postage on 3 preaddressed envelopes, and then send to Recipient 1 Envelope 1–containing the package, plus Envelope 2 (addressed to Recipient 2) and Envelope 3 (addressed to me).

However, when I asked the employee at the Post Office, her head nearly exploded. Due to 9/11 security regs., all packages above a certain weight must be brought into the post office. So she didn’t know how to accomplish this task.

Now, Recipient 1 works in a large office building, with a large and active mailroom. I worked in a similar place before, and mailing a package required nothing special from such an employee–the mailroom handled everything.

Recipient 2 works at home. Obviously, having the mail carrier simply pick up the package at her house would be easiest, but I don’t think a trip to the post office would be a total nightmare for her. However, I don’t know about FedEx, UPS, etc. … too much trouble. I’m trying to keep this simple for all the recipients.

How can I solve this problem? Did the postal worker just flip out unnecessarily? Is buying the proper postage and pre-stamping the preaddressed envelopes a reasonable notion? Is it going to cause nightmarish headaches for Recipient 1 or 2?

Check with the P.O. to be sure, but I was told that only stamped packages must be taken to the P.O. counter. If you buy electronic postage, there is no need to hand it to a regular person.

I do this at the automated postal center, which is in the lobby of my P.O. building.

Ah ha:

From here. It’s only stamped packages that ya have to worry about.