If your PDF is too big to email, you have two choices: shrink it or upload to a drive and share a link. Shrinking is faster, keeps recipients on the same workflow, and works on every email client. CrispPDF's email preset gets you under 10 MB on almost any document.
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Gmail and Outlook.com cap at 25 MB. Yahoo Mail caps at 25 MB. Corporate Exchange typically caps at 10 MB. iCloud Mail caps at 20 MB.
Not directly. Compress it to 10–20 MB with CrispPDF, or upload to Drive/OneDrive and share the link.