Easy — Chat Hoarding for Android + wireless share
Install the Chat Hoarding for Android APK. Tap Locate. Pick share mode (zip with media, chats only, or raw .crypt15). Chat Hoarding for Android hands the file to Android's system share sheet (Quick Share, Nearby, LocalSend, Drive, whatever your destination is). On the Mac, drop the zip into Chat Hoarding for Mac. Path of least resistance; no USB cable required.