You have two separate problems: Regarding playback, it’s impossible to tell whether or not it will be jumpy on your boss’ machine, unless he has the exact same unit as yours. I have found that really large MOV files are jumpy when using QT Player on my Windows laptop, but the jumpiness goes away when I reduce the size of the window. If he doesn’t have QT Player, then it will likely default to Windows Media Player which supports the following formats:
https://support.microsoft.com/kb/316992
Regarding sending large files, you could try one of two approaches.
1) Sign up for a free file storage service (like Dropbox.com) which typically start out at 2GB of space which you could share with your boss.
2) Use YouSendIt.com The free version only allows 200 MB, but for just a few bucks, you can send files up to 2GB in size via email. It does this by storing your content on their servers and providing a unique link to the file for a period of time.