OR
I would suggest that you start by deciding how important it is to you that you send files of that size. If you don't need to send high-res audio files, for example the files are recordings of a speech that you can understand at AM radio quality sound, then I'd recommend converting the files to a lower resolution. There are several utilities available to do that, I have used Music Match Jukebox for years, but I don't know if the free version allows that type of manipulation.
Splitting files up is a viable option also, but the person receiving will have to get the software and learn how to use it as well. In my view, that's solving one problem by creating another. It does work well, however.
If you are going to be pretty serious about sending these files in the future, I would follow the advice of JMarcomb and learn to use an ftp client. That may be particularly useful if the person who is receiving the stuff wants to choose how, when, and where they will download it. I recommend WSFTP, which is available as shareware on tucows.com; there are also other programs that work well. That method would permit you to upload the files to any webserver space you have (almost everyone has some, if only 10mb) and then email a link to that space that anyone can click on to download the file in full at their convenience.
I empathize with your frustration. If you need specific instructions, I'll help as much as I can. You're probably going to have to bite the bullet for a little while longer as your learning curve levels out, but it's worth the effort. (At least it has been for me!)