Hello Matt,
Thanks for using Apple Support Communities.
To troubleshoot this issue where you're unable to send files over Bluetooth between your Macs, please follow the steps outlined below.
Make sure the other device is Bluetooth enabled, turned on, and within range (up to 30 feet).
Make sure your computer is paired with the other device. Choose Apple menu > System Preferences, click Bluetooth, then check the status of the device in the list.
If the device is paired with your Mac and you still can’t send a file, try unpairing the device and then pairing with it again. To unpair the device, choose Apple menu > System Preferences, click Bluetooth, select the device, then click Remove. To pair with the device again, click Add.
Make sure you have permission to send a file to the device. You may need to enter a password. Check with the owner of the device.
Make sure the computer or device is set up to send or receive files (see instructions below).
Make sure you know which folder is being shared on the other computer or device.
Choose Apple menu > System Preferences, then click Sharing.
Select the Bluetooth Sharing checkbox.
Choose your options.
OS X Yosemite: Share files using Bluetooth
Cheers,
Alex H.