You Can't Get There From Here

After yesterday’s awesome discovery regarding FTP setups I tried to find other ways of setting this up. One option was to remote into the computer and email a file but with a caveat as I explained to the person requesting the solution:

Me: I think I have a solution, email yourself.
Him: How?
Me: Get subscription to and remote into the computer and send an email to another account.
Him: Great, how do I set it up?
Me: First you need to go home and setup the account.
Him: Why?
Me: It’s blocked from work.
Him: But I can remote home, can I use that?
Me: Probably, so, remote to your computer at home via VPN then setup the account on your laptop and use that to remote into your computer here.
Him: Is this the simplest way to do this?
Me: Using your office computer to remote into your home computer to setup a remote account to get a download to put on your laptop that then won’t be accessible from work but only from home or remoting to home. Yes.