I agree about the need being obviated but with one caveat: only if you’re using modern AES ZIP encryption. The old ZipCrypto which is the default (and only) option available in Windows ‘Compressed Folders’ uses ZipCrypto. You therefore need 7-Zip or WinZip or SecureZIP in order to harness modern AES.
Thus if you only have a ZIP application which only employs ZipCrypto then you might want to send an AxCrypt self-decrypting EXE because AxCrypt utilises proper encryption.
However many ZIP applications also support making a self-decrypting EXE and they allow you to use AES encryption too.
The main problem with sharing EXE files is Windows SmartScreen. If you download a non-signed EXE the recipient will get a warning suggesting the file is potentially unsafe.
I use an encrypted cloud where I can share a secure link. I can optionally require the recipient type in a pre-agreed password. Once the file has been downloaded it will automatically expire (unless I set it otherwise) and/or it will expire after a pre-defined date.
Modern PDFs (v1.6 and above) along with Microsoft Office 2013 both include strong encryption which are sufficient for most people. You can also put attachments within an encrypted PDF – something not many people realise.