What's more secure against Windows malware: latest Wine version, or oldest version for your distro?

[NM64]

I recently had a thought with regards to Windows malware running under Wine, that being what would be more secure:

• the latest version of Wine (due to having all of the newest security patches)
• the oldest version of Wine for your distro (due to having worse compatibility with Windows software)

I am aware that "Bottles" would be a better option for running Wine software in a secure manner, but the main issue is that there doesn't seem to be any native-Linux GUI-based software that you can just double-click on the likes of a checksum file and have it automatically hash and verify the file contents (associating a checksum file with GtkHash results in it hashing the actual file, not checking the hashes contained within the checksum file), thereby requiring me to install Wine along with HashCheck Shell Extension.

(One thing not mentioned in that thread is that the "other program" I spoke of, ExactFile, which works for creating checksum files via Wine but is much slower does not hash hidden files or folders annoyingly enough. There's also another program I've since discovered, md5summer, that can recursively hash hidden files and folders via Wine, but it takes quite a few more steps to create a checksum, it doesn't support files with unicode filenames which is a problem for a "certified weeb" like myself, it always asks if you want to associate md5summer with .md5 files, and it defaults to a .md5 extension even when selecting SHA1 format as well as incorrectly calling them MD5 checksums in the included comment lines in the resulting SHA1 checksum file.)