Won't I still be sending more than 1 file that way though?
Yes?
If its Gmail, upload it to Google Docs and make it public or viewable to a specific person/s.
What is setting the limit ? You could try a different email client.
Want it to be as easy as possible for them tbh. Is there not a format i can save it in that compresses it? No software online that can make the file size smaller?
pdf it?
Dropbox it.
Compress some of your images?
Try 7zip, I find that compresses more than normal zip.