If you’ve ever sent me a large file through email, you probably know how much I hate it. No one escapes a lecture! Just because GMail and other services give you gigabytes of storage, doesn’t mean that it’s okay to send really large attachments. I was happy to read that one my favorite blogs posted about the subject today. From the Microsoft Office Outlook Team Blog:
Putting any issues with your e-mail service provider’s limits on large messages aside, sending large attachments through e-mail is still a bad idea for a number of reasons.
In the post, Outlook Program Manager Ryan Gregg outlines a few of the reasons why you shouldn’t send large files via email – mail servers may reject large files, mailboxes may go over their quota, attachment bloat, attachments may be out of date, etc. He also outlines a number of alternatives, including SharePoint or a Shared File Server, Office Live, photo sharing sites like Flickr, and video sharing sites like YouTube.
When you use one of these alternative ways to share files with your friends, family, or colleagues you help them keep your mailbox and theirs clean, and you can be sure that your file will be available no matter what service or program your e-mail recipients are using.
I would add a couple more reasons to avoid sending large files: slow Internet connections and small devices. If I’m checking email on an unreliable connection, the last thing I want to do is wait for your images to download. If I’m checking email on my iPod touch or a cell phone, I might not be able to read the files anyway.
If you’re sending photos, why not stick them on Flickr and email a link? Same goes for video – use a site like YouTube. Some other alternatives include Box.net, Amazon S3, and SlideShare.
It doesn’t take a lot of extra effort to stick your file online somewhere first, so why not just do it? Send links to large files via email, not the files themselves!
MasterMaq's Blog 
I completely agree.
The problem is people are inherently lazy these days. Send To, Drop and drop, Insert File – all so convenient…
I find version control of documents/content/software to be the worst issue.
Ah yes, that’s another great reason to avoid sending files via email. It only kinda works with Word documents, which have a track changes feature.
Try using LeapFILE.
LeapFILE is a web based file transfer service provider and have just announced their release for Outlook Plugin and Microsoft Office. You can easily send your files as an email attachment but through LeapFILE’s platform and your recipients would automatically receive a unique and secure url to download. It also comes with audit trail tracking, email notification and end to end encryption for security and to let you keep track of the files you sent without all the hassles and restrictions of email.
Check out the Outlook Plugin on the website here: http://www.leapfile.com/Solutions/Outlook-Plug-in