Hey man, do you have access to microsoft outlook or microsoft office software? IF so, you can overcome the Windows 8.1 limitation with POP accounts using that. Otherwise, you can install any amount of freebie email software. Thunderbird/Mailbird/Dreammail are a few that come to mind.

Here is Microsofts stance on the issue, you may already have read it: http://windows.microsoft.com/en-IE/windows-8/pop-email-accounts

As for the 2nd issue. Would you not use something like GoogleDrive or Dropbox to upload the file(s) and then share the link (set it up as a private link so you keep things confidential if needs be). You can find those here: http://www.google.ie/drive/ https://www.dropbox.com/